1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

Query Query

Results

Date

67 reactions in Reaxys

2018-08-10 16h:26m:55s (UTC)

O

1. Query N

O

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='14377-63-0') AND (IDE.INCHI='BWSCMJUJHSJAEVUHFFFAOYSA-N') NOT (RX.RXRN=1284457))

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

H N

O

I

C

O

O

N

N

O

Rx-ID: 9444360 View in Reaxys 1/67 Yield 72 %, 22 %

Conditions & References Carbonylation of aryl iodide in the presence of secondary amines over Pd/CFP General procedure: To a 100-ml autoclave, were added aryl iodide (1.0 mmol), secondary amine (5.0 mmol), the catalyst (Pd: 0.78 molpercent), Cs2CO3(1.14 g, 3.5 mmol), LiI (9.0 mg, 0.0479 mmol) and toluene (5.0 ml).The autoclave was flushed by CO flow and pressurized to 4.0 MPa. The reaction was performed at 120C for the given time. The reaction mixture was extracted with ethyl acetate. Double carbonylation and mono carbonylation products were obtained by purification over silica column with the eluent of ethyl acetate/petroleum ether (60–90C) (v/v, 1:4). In the 12-run recycling test, the catalyst was separated by filtration and washed sequently by water, ethyl acetate and diethyl ether after each testing run. The catalyst was dried vacuum and then recycled into the next batch.

With caesium carbonate, lithium iodide in toluene, T= 120 °C , p= 30003Torr , Autoclave Chen, Bingfeng; Li, Fengbo; Huang, Zhijun; Lu, Tao; Yuan, Guoqing; Applied Catalysis A: General; vol. 481; (2014); p. 54 - 63 View in Reaxys With potassium phosphate, chloro-bridged dinuclear palladium in 1,4-dioxane, Time= 15h, T= 100 °C , p= 7600Torr Tsukada, Naofumi; Ohba, Yoichi; Inoue, Yoshio; Journal of Organometallic Chemistry; vol. 687; nb. 2; (2003); p. 436 - 443 View in Reaxys 2.3. The procedure for the aminocarbonylation reaction General procedure: reactionThe catalytic reactions were carried out in a 150 ml stainlesssteel autoclave equipped with a mechanical stirrer. Palladium cat-alyst (0.07 mmol), aryl iodide (10 mmol), amine (20 mmol), base(30 mmol) and solvent (15 ml) were loaded into the reactor. Theautoclave was purged three times with CO and pressurized to1.5 MPa with CO at room temperature.

The reaction was carriedout at 130C for appropriate time. After the reaction, the reactorwas cooled to room temperature and depressurized. The reac-tion mixture was centrifuged at 5000 rpm for 10 min and the clearsupernatant which was added naphthalene as an internal standardwas analyzed with GC. For the study of substrate scope, after com-pletion of the reaction, the catalyst was centrifuged at 5000 rpmfor 10 min and the clear supernatant was diluted with 20percent HCland extracted with diethyl ether. The organic layer was washedwith saturated NaHCO3and NaCl solutions, respectively, dried overanhydrous Na2SO4, and evaporated under vacuum after filtration.The residue obtained was purified by column chromatography (sil-ica gel, 200–300 mesh; petroleum-ethyl acetate, 20:1) to afford thepure products.

With triethylamine in N,N-dimethyl acetamide, T= 130 °C , Autoclave, High pressure, Green chemistry Mei, Hui; Hu, Jianglin; Xiao, Se; Lei, Yizhu; Li, Guangxing; Applied Catalysis A: General; vol. 475; (2014); p. 40 - 47 View in Reaxys

89 %Chromat., 11 %Chromat.

3 With 1,8-diazabicyclo[5.4.0]undec-7-ene in toluene, T= 100 °C , p= 22502.3Torr , Autoclave, Inert atmosphere Urbán, Béla; Szabó, Péter; Srankó, Dávid; Sáfrán, György; Kollár, László; Skoda-Földes, Rita; Molecular Catalysis; vol.

445; (2018); p. 195 - 205 View in Reaxys

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

O

H N

O

O

O

N

O

Rx-ID: 10242409 View in Reaxys 2/67 Yield 96 %

Conditions & References 1 : Example 1; 1-(Phenylglyoxylyl)piperidine Methyl phenylglyoxylate (12.50 Kg, 76.1 mol, 1 eq) was added dropwise to a stirred mixture of piperidine (19.45 Kg, 228 mol, 3 eq) and methanol (5.0 L) for 3.5 hours to maintain the temperature at 45-55° C. The mixture was stirred at the same temperature for 0.5 hour and kept overnight at +4° C. The precipitated solid was filtered off, washed on the filter with cold methanol (5 L) and dried under reduced pressure to a constant weight to give 15.90 Kg (96percent) of 1-(phenylglyoxylyl)piperidine with 99.9percent purity by GC. in methanol, T= 4 - 55 °C Patent; ISP INVESTMENTS INC.; US2004/180928; (2004); (A1) English View in Reaxys

96 %

1 :methyl phenylglyoxylate (12.50 Kg, 76.1 mol, 1 eq) was added dropwise to a stirred mixture of piperidine (19.45 Kg, 228 mol, 3 eq) and methanol (5.0 L) for 3.5 hours to maintain the temperature at 45-55° C. The mixture was stirred at the same temperature for 0.5 hour and kept overnight at +4° C. The precipitated solid was filtered off, washed on the filter with cold methanol (5 L) and dried under reduced pressure to a constant weight to give 15.90 kg (96percent) of 1-(phenylglyoxylyl)piperidine with 99.9percent purity by GC. in methanol, T= 4 - 55 °C Patent; ISP INVESTMENTS INC.; US2004/176412; (2004); (A1) English View in Reaxys

85 %

1 : Example 1. Synthesis of Phenyl-2-(piperidin-1-yl)ethane-1,2-dione (compound of formula (3)).

500 g (3.05 mol, 1 eq.) of methyl benzoylformate (compound of formula (2) and 259.] g (3.05 mol, 1 eq.) of piperidine were vigorously stirred in a 2 L batch glass reactor at 105 °C for 8 h. The reaction mixture was then cooled to room temperature, triturated in petroleum spirit 40-60 and filtered to give 563 g (85percent) of compound of formula (3) as an off-white solid. ‘H NMR (CDCI3, 400 MHz): 6 = 7.92-7.98 (m, 2H), 7.61-7.67 (m, 1H), 7.51 3, 2H, i = 7.7 Hz), 3.66-3.75 (m, 2H),3.25-3.33 (m, 2H), 1.66-1.74 (m, 4H), 1.52-1.56 (m, 2H) ppm; “C NMR (CDCI3, 100.6 MHz): 6 = 191.9, 165.4, 134.6,133.2, 129.5, 129.0, 47.0, 42.1, 26.1, 25.4, 24.3 ppm. ESl-HRMS: [M÷H] calcd: 218.1176, found: 218.1178. MP: 104.7-106.3 °C. , Time= 8h, T= 105 °C Patent; UNIVERSITÉ DE LIÈGE; MONBALIU, Jean-Christophe; GERARDY, Romaric; (30 pag.); WO2018/50546; (2018); (A1) English View in Reaxys

83 %

1.a : a). Preparation of Intermediate 1 To the dry and clean 3L added three-mouth flask, add 1.0Lg methanol. Start the stirring. Add 0.37 kg piperidine, 0.59 kg methyl benzoylformate. Heat to 50 - 55 °C and maintain temperature and react for 2 hours. Afterwards, TLC monitoring reaction process (GF254 silica gel plate; developing solvent: ethyl acetate/petroleum ether=1/2), when the raw material point disappears to stop reaction, discharging to the clean and dry cake in the temperature slowly drops to 0 - 5 °C, make the solid fully separate out, filtering, the filter cake is pre-cooled to - 5 - 0 °C methanol stirs washes 2 time, each time consumption 0.5 kg, 60 °C blast drying overnight, to obtain 0.65 kg of intermediate 1, white solid, by HPLC area normalization method to the detection of the intermediate 1 content of 99.50percent, yield 83percent. in methanol, Time= 2h, T= 50 - 55 °C , Large scale Patent; Hefei Lifeon Pharmaceutical Co., Ltd.; Pei, Lin; Li, Bing; Hu, Dejin; Chen, Jun; Gao, Meihua; Ji, Junqiu; (11 pag.); CN106349151; (2017); (A) Chinese View in Reaxys

82 %

in toluene, Time= 3h, Heating

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

Moehrle; Rohn; Westle; Pharmazie; vol. 61; nb. 5; (2006); p. 391 - 399 View in Reaxys 30.3 %

Representative procedure for synthesis of benzoylformamides except BFA-iPA: General procedure: Methyl benzoylformate (10mmol) in methanol (10mL) was added dropwise to a stirred mixture of amine (30mmol) and methanol (20mL) at 55°C and then stirred for 3h, distilled to concentrate the solution, and crystallized in the refrigerator. The crystal was filtered, washed with cooled methanol, and dried in vacuum to give white crystals. in methanol, Time= 3h, T= 55 °C He, Ming-Hui; Su, Mei-Lin; Yu, Zhao-Hui; Chen, Guang-Xue; Zeng, Zhao-Hua; Yang, Jian-Wen; Chinese Chemical Letters; vol. 26; nb. 1; (2015); p. 21 - 25 View in Reaxys

H N

O

N

O

Rx-ID: 38300023 View in Reaxys 3/67 Yield 86 %

Conditions & References B: Standard reaction procedure terminal alkyne General procedure: B: Standard reaction procedure terminal alkyne: SeO2 (1.0 mmol) was added to a solutionof terminal alkyne (1.0 mmol) in dioxan (1 ml) followed by the addition of 10molpercent of H2SO4 and amine (1.0 mmol). The reaction mixturewas then heated at 80oC for 10-12 h and the product formation wasmonitored by TLC. After completion, reaction mixture was partioned with waterethyl acetate, extracted with ethyl acetate (3 x 50ml). The combined organiclayers were washed with brine solution, concentrated on rotary evaporator andpurified by column chromatography using ethyl acetate and hexane to affordcorresponding pure products. Spectral data:N,N-diethylbenzamide (3a): 1H NMR (CDCl3,400 MHz): H δ 7.26-7.40 (m,5H), 3.54 (s, 2H), 3.25 (s, 2H), 1.25(s, 3H), 1.10 (s, 3H); 13CNMR (CDCl3, 100 MHz): δc 171.32, 137.33, 129.10, 128.41, 126.28, 42.29, 39.23,14.23, 12.93. ESIMS: m/z 178.12 [M+H]+, Yield 90percent.

With selenium(IV) oxide, sulfuric acid in 1,4-dioxane, T= 80 °C , Reagent/catalyst Meena, Samdarshi; Singh, Rohit; Vishwakarma, Ram A.; Aga, Mushtaq A.; Jain, Shreyans K.; Tetrahedron Letters; vol.

57; nb. 33; (2016); p. 3715 - 3717 View in Reaxys

78 %

With trimethylsilyl trifluoromethanesulfonate, iodine in dimethyl sulfoxide, Time= 8h, T= 80 °C Deshidi, Ramesh; Kumar, Manjeet; Devari, Shekaraiah; Shah, Bhahwal Ali; Chemical Communications; vol. 50; nb. 67; (2014); p. 9533 - 9535 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium carbonate in neat (no solvent), Time= 5h, Heating, Green chemistry Dutta, Pratip Kumar; Dhar, Basabbijayi; Sen, Subhabrata; New Journal of Chemistry; vol. 42; nb. 14; (2018); p. 12062 12071 View in Reaxys

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

H N

HO

HO

O

N

O

Rx-ID: 48110452 View in Reaxys 4/67 Yield 99 %Chromat.

Conditions & References With [Cu(μOH)(tmeda)]2Cl2, 9-azanoradamantane N-oxyl, oxygen in tetrahydrofuran, Time= 2h, T= 23 °C , Molecular sieve Kataoka, Kengo; Wachi, Keiju; Jin, Xiongjie; Suzuki, Kosuke; Sasano, Yusuke; Iwabuchi, Yoshiharu; Hasegawa, JunYa; Mizuno, Noritaka; Yamaguchi, Kazuya; Chemical Science; vol. 9; nb. 21; (2018); p. 4756 - 4768 View in Reaxys

O

N

O

Rx-ID: 6456265 View in Reaxys 5/67 Yield 72%

Conditions & References 21 : Example 17 2-(lH-imidazol-l-yl)-l-phenylethanone (IBp) General procedure: Example 16 Experimental procedure for the preparation of a-substituted carbonyl compounds (IBp-w) (0117) To a stirred solution of styrene (1 mmol, 104 mg) in dry DMSO (10 mL) at 0 °C was added NBS (1 mmol, 178 mg) followed by slow addition of amine III (1 mmol). The reaction mixture was then allowed to stir at 25 °C for 8 hours (monitored

by TLC). After completion, the reaction mixture was diluted with water and EtOAc. The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 20 mL). The combined organic extracts were repeatedly washed with saturated brine solution, dried over anhyd. Na2S04 and concentrated under reduced pressure to give crude products which were purified by column chromatography [silica gel (230-400 mesh)] using petroleum ether: EtOAc (6:4) as eluent to afford corresponding asubstituted carbonyl compounds (IBp-w) in good yield. (0118) Example 17 2-(lH-imidazol-l-yl)-l-phenylethanone (IBp) (0119) Yield: 86percent (160 mg); Colorless solid; mp: 117-119 °C; 1δ NMR (200 MHz, CDC13): δ 5.41 (s, 2H), 6.88-6.99 (m, IH), 7.09-7.15 (m, IH), 7.45-7.59 (m, 3H), 7.60-7.75 (m, IH), 7.90-8.02 (m, 2H); 13C NMR (50 MHz, CDC13): δ 52.4, 120.3, 127.9, 129.1, 129.4, 134.4, 138.1, 191.5: HRMS calcd for [(Cl lH10N2O+Na)+] 209.0691; found: 209.0695.

With N-Bromosuccinimide in dimethyl sulfoxide, Time= 8h, T= 0 - 25 °C Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; SUDALAI, Arumugam; PRASAD, Pragati Kishore; REDDI, Rambabu; (31 pag.); WO2017/77550; (2017); (A1) English View in Reaxys Oxophenylessigsaeure, Piperidin, Thionylchlorid/Pyridin Johansson et al.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 30; (1976); p. 383,387 View in Reaxys Oxophenylessigsaeure, Piperidin, Thionylchlorid, Py. Johansson et al.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 30; (1976); p. 383,387 View in Reaxys Phenylglyoxylsaeure, Piperidin, Ae. Earle et al.; Journal of the Chemical Society [Section] C: Organic; (1969); p. 2093,2096 View in Reaxys Aus Benzoylameisensaeure-aethylester u. Piperidin

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

Muchowski,J.M.; Tetrahedron Letters; (1966); p. 1773 - 1778 View in Reaxys 1-<δ-Brom-phenylacetyl>-piperidin, Pyridin-1-oxid, Toluol, Erhitzen Earle et al.; Journal of the Chemical Society [Section] C: Organic; (1969); p. 2093,2096 View in Reaxys aus dem Ester (IIa), Piperidin und Sauerstoff Glushkov et al.; Zhurnal Organicheskoi Khimii; vol. 10; (1974); p. 304,304,306 View in Reaxys

H N

O

I

C

O

N

O

Rx-ID: 28621747 View in Reaxys 6/67 Yield

Conditions & References

98 %

With potassium carbonate in N,N-dimethyl-formamide, Time= 12h, T= 90 °C , p= 15201Torr , Autoclave Molla, Rostam Ali; Iqubal, Md. Asif; Ghosh, Kajari; Roy, Anupam Singha; Kamaluddin; Islam, Sk. Manirul; RSC Advances; vol. 4; nb. 89; (2014); p. 48177 - 48190 View in Reaxys

89 %

With IPrCuI, caesium carbonate, 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride in 1,4-dioxane, Time= 10h, T= 100 °C , p= 22502.3Torr Liu, Jianming; Zhang, Rongzhao; Wang, Shoufeng; Sun, Wei; Xia, Chungu; Organic Letters; vol. 11; nb. 6; (2009); p. 1321 - 1324 View in Reaxys

48 %

With PdCl(N,N-dimethylbenzylamine(-H)-δ2N,C)(C3H2N2(2,6-iPr2C6H3)2), potassium carbonate in 1,4-dioxane, Time= 12h, T= 80 °C , p= 30003Torr , Autoclave Zhang, Chunyan; Liu, Jianhua; Xia, Chungu; Organic and Biomolecular Chemistry; vol. 12; nb. 47; (2014); p. 9702 - 9706 View in Reaxys With triethylamine in N,N-dimethyl-formamide, Time= 3h, T= 100 °C , p= 22502.3Torr , Autoclave Papp; Szabó; Srankó; Sáfrán; Kollár; Skoda-Földes; RSC Advances; vol. 7; nb. 70; (2017); p. 44587 - 44597 View in Reaxys

H N

O

N

O

Rx-ID: 45000427 View in Reaxys 7/67 Yield 56 %

Conditions & References With tert.-butylhydroperoxide, copper(l) iodide in neat (no solvent), Time= 24h, T= 50 °C Liu, Fuyan; Zhang, Kuan; Liu, Yanfeng; Chen, Shan; Chen, Yiping; Zhang, Dela; Lin, Chunfu; Wang, Bo; RSC Advances; vol. 7; nb. 12; (2017); p. 7158 - 7162

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

View in Reaxys

O H 2N

Cl

H

O

N

O

Rx-ID: 45103541 View in Reaxys 8/67 Yield

Conditions & References

44 %

With tert.-butylhydroperoxide, tetra-(n-butyl)ammonium iodide, potassium carbonate in water, dimethyl sulfoxide, T= 50 °C Wang, Dan; Zhang, Kuan; Jia, Luhan; Zhang, Danting; Zhang, Yue; Cheng, Yujia; Lin, Chang; Wang, Bo; Organic and Biomolecular Chemistry; vol. 15; nb. 16; (2017); p. 3427 - 3434 View in Reaxys

H N

O

O

O

N

O

Rx-ID: 33516416 View in Reaxys 9/67 Yield 85 %

Conditions & References Catalytic studies General procedure: In a typical experiment, a mixture of phenylglyoxal monohydrate (0.11mL, 1.0mmol), pyrrolidine (0.246mL, 3.0mmol), and diphenyl ether (0.07mL) as an internal standard in toluene (4mL) was added into a 25mL flask containing the pre-determining amount of Cu-MOF-74 catalyst. The catalyst amount was calculated with respect to the copper/phenylglyoxal molar ratio. The reaction mixture was stirred at 80°C for 120min. Reaction conversion was monitored by withdrawing aliquots from the reaction mixture at different time intervals, quenching with aqueous KOH (1mL). The organic components were then extracted into ethyl acetate (2mL), dried over anhydrous Na2SO4, analyzed by GC with reference to diphenyl ether. The product identity was further confirmed by GC–MS and 1H NMR. To investigate the recyclability of Cu-MOF-74, the catalyst was separated from the reaction mixture by simple filtration, washed with copious amounts of DMF and methanol, dried 150°C under vacuum in 2h, and reused if necessary. For the leaching test, a catalytic reaction was stopped after 20min, analyzed by GC, and filtered to remove the solid catalyst. The reaction solution was then stirred for a further 100min. Reaction progress, if any, was monitored by GC as previously described.

With Cu metal-organic framework-74 in toluene, Time= 2h, T= 80 °C Truong, Thanh; Dang, Giao H.; Tran, Nam V.; Truong, Ngoc T.; Le, Dung T.; Phan, Nam T.S.; Journal of Molecular Catalysis A: Chemical; vol. 409; (2015); p. 110 - 116 View in Reaxys

84 %

With dimethyl sulfoxide, Time= 2.5h, T= 80 °C Mupparapu, Nagaraju; Khan, Shahnawaz; Battula, Satyanarayana; Kushwaha, Manoj; Gupta, Ajai Prakash; Ahmed, Qazi Naveed; Vishwakarma, Ram A.; Organic Letters; vol. 16; nb. 4; (2014); p. 1152 - 1155 View in Reaxys

83 %

in dimethyl sulfoxide, Time= 2h, T= 80 °C , Temperature, Solvent Dutta, Sayan; Kotha, Surya Srinivas; Sekar, Govindasamy; RSC Advances; vol. 5; nb. 58; (2015); p. 47265 - 47269 View in Reaxys

82 %

in dimethyl sulfoxide, Time= 1.5h, T= 25 °C Prasad, Pragati K.; Reddi, Rambabu N.; Sudalai, Arumugam; Organic Letters; vol. 18; nb. 3; (2016); p. 500 - 503

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

View in Reaxys 81 %

With pyridine, oxygen, copper(I) bromide in toluene, Time= 12h, T= 90 °C , p= 760.051Torr Zhang, Chun; Zong, Xiaolin; Zhang, Liangren; Jiao, Ning; Organic Letters; vol. 14; nb. 13; (2012); p. 3280 - 3283 View in Reaxys

76 %

General procedure General procedure: To a solution of AuBr3 (10.9mg, 5molpercent), glyoxal derivative 1 (0.5mmol) and secondary amine 2 (0.75mmol) in CH2Cl2 (2mL) in a 10mL Schlenk tube. The resulting solution was stirred at 60°C overnight. After cooling to room temperature, the resulting mixture was filtered through a pad of celite. The volatile compounds were removed in vacuum and the residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate=10:1–4:1) to give compounds 3.

With gold(III) bromide, oxygen in dichloromethane, Time= 12h, T= 60 °C , Schlenk technique, Catalytic behavior, Mechanism, Temperature, Reagent/catalyst, Solvent Shao, Ying; Wu, Zhuhong; Miao, Chunbao; Liu, Li; Journal of Organometallic Chemistry; vol. 767; (2014); p. 60 - 64 View in Reaxys

72 %

With air in toluene, Time= 2h, T= 60 °C Mupparapu, Nagaraju; Battini, Narsaiah; Battula, Satyanarayana; Khan, Shahnawaz; Vishwakarma, Ram A.; Ahmed, Qazi Naveed; Chemistry - A European Journal; vol. 21; nb. 7; (2015); p. 2954 - 2960 View in Reaxys

58 %

With nitroacetic acid ethyl ester, potassium iodide in ethanol, T= 20 °C , Electrolysis Li, Yanan; Gao, Huihui; Zhang, Zhenlei; Qian, Peng; Bi, Meixiang; Zha, Zhenggen; Wang, Zhiyong; Chemical Communications; vol. 52; nb. 55; (2016); p. 8600 - 8603 View in Reaxys With selenium(IV) oxide in 1,4-dioxane, T= 80 °C Meena, Samdarshi; Singh, Rohit; Vishwakarma, Ram A.; Aga, Mushtaq A.; Jain, Shreyans K.; Tetrahedron Letters; vol.

57; nb. 33; (2016); p. 3715 - 3717 View in Reaxys

H N

O

O

N

O

Rx-ID: 33778956 View in Reaxys 10/67 Yield 92 %

Conditions & References With tert.-butylhydroperoxide, N-iodo-succinimide in water, acetonitrile, Time= 1h, T= 20 °C Lamani, Manjunath; Prabhu, Kandikere Ramaiah; Chemistry - A European Journal; vol. 18; nb. 46; (2012); p. 14638 14642 View in Reaxys

91 %

With tert.-butylhydroperoxide, iodine, Time= 8h, T= 20 - 25 °C Zhang, Xiaobin; Wang, Lei; Green Chemistry; vol. 14; nb. 8; (2012); p. 2141 - 2145 View in Reaxys

90 %

With N-iodo-succinimide, oxygen, copper(I) bromide in toluene, T= 20 °C Zhang, Juan; Wei, Ying; Lin, Shaoxia; Liang, Fushun; Liu, Pengjun; Organic and Biomolecular Chemistry; vol. 10; nb. 46; (2012); p. 9237 - 9242 View in Reaxys

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

90 %

With bis[(tetrabutylammonium) di-μ-iodo-diiododicuprate(I)] complex, oxygen in water, Time= 0.166667h, T= 60 °C , Microwave irradiation Nekkanti, Shalini; Veeramani, Karuna; Praveen Kumar, Niggula; Shankaraiah, Nagula; Green Chemistry; vol. 18; nb. 11; (2016); p. 3439 - 3447 View in Reaxys

86 %

With tert.-butylhydroperoxide, iodine, benzoic acid Zhao, Qiong; Miao, Tao; Zhang, Xiaobin; Zhou, Wei; Wang, Lei; Organic and Biomolecular Chemistry; vol. 11; nb. 11; (2013); p. 1867 - 1873 View in Reaxys

85 %

A: Standard reaction procedure arylaldehydes or phenylacetones General procedure: A: Standard reaction procedure arylaldehydes or phenylacetones: SeO2 (1.0 mmol) was added to a solution ofarylaldeydes or phenylacetones or terminal alkyne (1.0 mmol) in dioxan (1 ml) andamine (1.0 mmol). The reaction mixture was then heated at 80oC for10-12 h and the product formation was monitored by TLC. After completion,reaction mixture was partioned with water ethyl acetate, extracted with ethylacetate (3 x 50ml). The combined organic layers were washed with brinesolution, concentrated on rotary evaporator and purified by columnchromatography using ethyl acetate and hexane to afford corresponding pureproducts.

With selenium(IV) oxide in 1,4-dioxane, T= 80 °C Meena, Samdarshi; Singh, Rohit; Vishwakarma, Ram A.; Aga, Mushtaq A.; Jain, Shreyans K.; Tetrahedron Letters; vol.

57; nb. 33; (2016); p. 3715 - 3717 View in Reaxys

83 %

With iodine, oxygen in 1,4-dioxane, Time= 16h, T= 90 °C , Green chemistry Guo, Shiyu; Fang, Zheng; Yang, Zhao; Liu, Chengkou; Dai, Zhongxue; Zhao, Lihuan; Guo, Kai; RSC Advances; vol. 6; nb. 2; (2016); p. 1503 - 1507 View in Reaxys

81 %

With SBA-16-pro-Cu(I), air in ethyl acetate, Time= 16h, T= 50 °C , Reagent/catalyst, Temperature, Time, Solvent Zhang, Xueyao; Yang, Honglei; Huo, Yong; Li, Jing; Ma, Jianxin; Ma, Jiantai; Dalton Transactions; vol. 45; nb. 21; (2016); p. 8972 - 8983 View in Reaxys

70 %

With oxygen, tetra-(n-butyl)ammonium iodide in ethanol, Time= 3h, T= 20 °C , Electrochemical reaction Zhang, Zhenlei; Su, Jihu; Zha, Zhenggen; Wang, Zhiyong; Chemical Communications; vol. 49; nb. 79; (2013); p. 8982 8984 View in Reaxys

64 %

With tert.-butylhydroperoxide, water, iodine in isopropyl alcohol, Time= 13h, T= 20 °C Wei, Wei; Shao, Ying; Hu, Huayou; Zhang, Feng; Zhang, Chao; Xu, Yuan; Wan, Xiaobing; Journal of Organic Chemistry; vol. 77; nb. 17; (2012); p. 7157 - 7165 View in Reaxys

32 %

preparation of α-ketoamides General procedure: All chemicalswere purchased from common chemical supply companies and used withoutfurther purification. A flame fried round bottom flask with magnetic stir bar was charged with substituted acetophenone (1 equiv) in anhydrous toluene(0.4 M). To this was added piperidine (1.1 equiv), and CuI (0.1 equiv). The solution was placed under a molecular oxygen atmosphere and heated to 65 Cfor 5 h (as monitored by thin layer chromatography [TLC]). The reaction mixture was extracted with ethyl acetate, washed with water and brine, and the organic layer dried over sodium sulfate. The crude mixture was filtered,concentrated in vacuo and purified via column chromatography (30–50:70–50 ethyl acetate/hexanes) to afford the desired a-ketoamide as an off white solid (25–94percent).

With copper(l) iodide, oxygen in toluene, Time= 5h, T= 65 °C Wedler, Henry B.; Palazzo, Teresa A.; Pemberton, Ryan P.; Hamann, Christian S.; Kurth, Mark J.; Tantillo, Dean J.; Bioorganic and Medicinal Chemistry Letters; vol. 25; nb. 19; (2015); p. 4153 - 4157 View in Reaxys

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

195.6 mg

α-Ketoamides; Typical Procedure General procedure: The 1-arylethanol (1 mmol) was added to a mixture of CuI (30 molpercent) and TBHP (5–6 M in decane, 2 equiv) in a reaction tube at r.t. under an O2 atm (O2 balloon). The resulting mixture was stirred at 50 °C for 3– 8 h (TLC monitoring). After complete disappearance of the 1-arylethanol, the amine (3 equiv) was added at r.t. and the mixture was stirredat 50 °C until completion of the reaction. The mixture was allowed to cool to r.t. and then filtered through Celite. The filter cake was rinsed with CH2Cl2 and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexanes–EtOAc) to afford pure δ-ketoamide 3.

With copper(l) iodide, oxygen in neat (no solvent), Time= 16h, T= 50 °C , Mechanism, Reagent/catalyst, Solvent Sharma, Nidhi; Kotha, Surya Srinivas; Lahiri, Nabajit; Sekar, Govindasamy; Synthesis (Germany); vol. 47; nb. 5; (2015); p. 726 - 736; Art.No: SS-2014-T0695-OP View in Reaxys With tert.-butylhydroperoxide, sodium iodide in water, Time= 6h, T= 20 °C Ramanathan, Mani; Kuo, Chun-Kai; Liu, Shiuh-Tzung; Organic and Biomolecular Chemistry; vol. 14; nb. 48; (2016); p.

11446 - 11453 View in Reaxys

O

O

N

N

O

Rx-ID: 33778965 View in Reaxys 11/67 Yield 96 %

Conditions & References With tert.-butylhydroperoxide, T= 20 °C Zhang, Xiaobin; Wang, Lei; Green Chemistry; vol. 14; nb. 8; (2012); p. 2141 - 2145 View in Reaxys

89 %

With tert.-butylhydroperoxide Zhao, Qiong; Miao, Tao; Zhang, Xiaobin; Zhou, Wei; Wang, Lei; Organic and Biomolecular Chemistry; vol. 11; nb. 11; (2013); p. 1867 - 1873 View in Reaxys

63 %

2. Typical procedure for the α-oxidation of compound 1 General procedure: Pyrrolidine (123 μL, 1.5 mmol) was added to a solution of δ-keto-amine 1 (0.3mmol) and TEMPO (4.7 mg, 0.03 mmol) in MeCN (1 mL) under O2 (balloon pressure) atmosphere. The reaction mixture was then stirred at room temperature for 20h and the product was monitored by TLC. The reaction mixture was then concentrated and purified by column chromatography (n-heptane/EtOAc) to afford the corresponding product.

With pyrrolidine, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 20h, T= 50 °C Yu, Lu; Somfai, Peter; Synlett; vol. 27; nb. 18; (2016); p. 2587 - 2590; Art.No: ST-2016-B0315-L View in Reaxys With piperidine, oxygen, tetra-(n-butyl)ammonium iodide in ethanol, T= 20 °C , Electrochemical reaction Zhang, Zhenlei; Su, Jihu; Zha, Zhenggen; Wang, Zhiyong; Chemical Communications; vol. 49; nb. 79; (2013); p. 8982 8984 View in Reaxys

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10/30

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

O

O

N

O

Rx-ID: 37410880 View in Reaxys 12/67 Yield

Conditions & References Reaction Steps: 2 1: dimethyl sulfoxide; iodine / 1 h / 80 °C 2: dimethyl sulfoxide / 2.5 h / 80 °C With iodine, dimethyl sulfoxide Mupparapu, Nagaraju; Khan, Shahnawaz; Battula, Satyanarayana; Kushwaha, Manoj; Gupta, Ajai Prakash; Ahmed, Qazi Naveed; Vishwakarma, Ram A.; Organic Letters; vol. 16; nb. 4; (2014); p. 1152 - 1155 View in Reaxys Reaction Steps: 2 1: acetic acid; copper(I) oxide; oxygen / 21 h / 120 °C 2: acetic acid; copper(I) oxide; oxygen / 120 °C With copper(I) oxide, oxygen, acetic acid Zhou, Mingxin; Song, Qiuling; Synthesis (Germany); vol. 46; nb. 14; (2014); p. 1853 - 1858; Art.No: SS-2014-C0127-ST View in Reaxys Reaction Steps: 2 1: selenium(IV) oxide 2: selenium(IV) oxide / 1,4-dioxane / 80 °C With selenium(IV) oxide in 1,4-dioxane Meena, Samdarshi; Singh, Rohit; Vishwakarma, Ram A.; Aga, Mushtaq A.; Jain, Shreyans K.; Tetrahedron Letters; vol.

57; nb. 33; (2016); p. 3715 - 3717 View in Reaxys

H N

O

N

O

Rx-ID: 39802571 View in Reaxys 13/67 Yield 78 %

Conditions & References With tert.-butylhydroperoxide, iodine in neat (no solvent), Time= 8h, T= 20 °C , Green chemistry, Reagent/catalyst Deshidi, Ramesh; Devari, Shekaraiah; Shah, Bhahwal Ali; European Journal of Organic Chemistry; vol. 2015; nb. 7; (2015); p. 1428 - 1432 View in Reaxys

72 %

With N-Bromosuccinimide in dimethyl sulfoxide, Time= 10h, T= 0 - 25 °C , regioselective reaction Prasad, Pragati K.; Reddi, Rambabu N.; Sudalai, Arumugam; Organic Letters; vol. 18; nb. 3; (2016); p. 500 - 503 View in Reaxys

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11/30

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

O

N

O

Rx-ID: 40452320 View in Reaxys 14/67 Yield

Conditions & References Reaction Steps: 2 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; iodine / dimethyl sulfoxide / 3.5 h / 80 °C 2: dimethyl sulfoxide / 2 h / 80 °C With iodine, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide Dutta, Sayan; Kotha, Surya Srinivas; Sekar, Govindasamy; RSC Advances; vol. 5; nb. 58; (2015); p. 47265 - 47269 View in Reaxys Reaction Steps: 2 1: N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethyl sulfoxide / 4 h / 0 - 25 °C 2: dimethyl sulfoxide / 6 h / 0 - 25 °C With N-Bromosuccinimide, 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethyl sulfoxide Prasad, Pragati K.; Reddi, Rambabu N.; Sudalai, Arumugam; Organic Letters; vol. 18; nb. 3; (2016); p. 500 - 503 View in Reaxys Reaction Steps: 3 1: N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethyl sulfoxide / 4 h / 0 - 25 °C 2: dimethyl sulfoxide / 4 h / 25 °C 3: dimethyl sulfoxide / 1.5 h / 25 °C With N-Bromosuccinimide, 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethyl sulfoxide Prasad, Pragati K.; Reddi, Rambabu N.; Sudalai, Arumugam; Organic Letters; vol. 18; nb. 3; (2016); p. 500 - 503 View in Reaxys

O

O

Br

N

O

Rx-ID: 41826134 View in Reaxys 15/67 Yield

Conditions & References Reaction Steps: 2 1: dimethyl sulfoxide / 4 h / 25 °C 2: dimethyl sulfoxide / 1.5 h / 25 °C in dimethyl sulfoxide Prasad, Pragati K.; Reddi, Rambabu N.; Sudalai, Arumugam; Organic Letters; vol. 18; nb. 3; (2016); p. 500 - 503 View in Reaxys

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

H N

O

O

Br

N

O

Rx-ID: 41826135 View in Reaxys 16/67 Yield

Conditions & References

84 %

in dimethyl sulfoxide, Time= 6h, T= 0 - 25 °C Prasad, Pragati K.; Reddi, Rambabu N.; Sudalai, Arumugam; Organic Letters; vol. 18; nb. 3; (2016); p. 500 - 503 View in Reaxys

H N

O

HO

N

O

Rx-ID: 42101335 View in Reaxys 17/67 Yield

Conditions & References

89 %

Stage 1: With sulfuric acid, dihydrogen peroxide, potassium iodide in water, N,N-dimethyl-formamide, Time= 0.05h, T= 60 °C , Flow reactor, Green chemistry Stage 2: in water, N,N-dimethyl-formamide, T= 60 °C , Flow reactor, Green chemistry Liu, Chengkou; Fang, Zheng; Yang, Zhao; Li, Qingwen; Guo, Shiyu; Guo, Kai; RSC Advances; vol. 6; nb. 30; (2016); p.

25167 - 25172 View in Reaxys

H N

O

O

N

O

Rx-ID: 43022555 View in Reaxys 18/67 Yield 65 %

Conditions & References A: Standard reaction procedure arylaldehydes or phenylacetones General procedure: A: Standard reaction procedure arylaldehydes or phenylacetones: SeO2 (1.0 mmol) was added to a solution ofarylaldeydes or phenylacetones or terminal alkyne (1.0 mmol) in dioxan (1 ml) andamine (1.0 mmol). The reaction mixture was then heated at 80oC for10-12 h and the product formation was monitored by TLC. After completion,reaction mixture was partioned with water ethyl acetate, extracted with ethylacetate (3 x 50ml). The combined organic layers were washed with brinesolution, concentrated on rotary evaporator and purified by columnchromatography using ethyl acetate and hexane to afford corresponding pureproducts.

With selenium(IV) oxide in 1,4-dioxane, T= 80 °C Meena, Samdarshi; Singh, Rohit; Vishwakarma, Ram A.; Aga, Mushtaq A.; Jain, Shreyans K.; Tetrahedron Letters; vol.

57; nb. 33; (2016); p. 3715 - 3717 View in Reaxys

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13/30

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

O

H N

H N

O

N

O

Rx-ID: 43026000 View in Reaxys 19/67 Yield

Conditions & References

70 %

With oxygen, copper diacetate, dibenzoyl peroxide in dimethyl sulfoxide, Time= 12h, T= 110 °C Liu, Xing-Xing; Wu, Zhao-Yang; He, Yong-Qin; Zhou, Xiao-Qiang; Hu, Ting; Ma, Chao-Wei; Huang, Guo-Sheng; Advanced Synthesis and Catalysis; vol. 358; nb. 15; (2016); p. 2385 - 2391 View in Reaxys

H N

O

HO

N

O

Rx-ID: 43220869 View in Reaxys 20/67 Yield

Conditions & References

85 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, potassium carbonate, copper(I) bromide in dimethyl sulfoxide, Time= 12h, T= 70 °C Liu, Chengkou; Yang, Zhao; Guo, Shiyu; Zeng, Yu; Zhu, Ning; Li, Xin; Fang, Zheng; Guo, Kai; Organic and Biomolecular Chemistry; vol. 14; nb. 36; (2016); p. 8570 - 8575 View in Reaxys

O

O

O

N

O N

N

O

Rx-ID: 43496819 View in Reaxys 21/67 Yield 84 %

Conditions & References With copper(II) bis(trifluoromethanesulfonate) in tetrahydrofuran, Time= 12h, T= 20 °C , Inert atmosphere, Reagent/catalyst, Solvent, Temperature Shen, Guodong; Zhao, Lingyu; Wang, Yichen; Zhang, Tongxin; RSC Advances; vol. 6; nb. 82; (2016); p. 78307 - 78310 View in Reaxys

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14/30

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

O

N

O

Rx-ID: 44087772 View in Reaxys 22/67 Yield

Conditions & References Reaction Steps: 2 1: iodine; tert.-butylhydroperoxide; pyridine / water / 10 h / 80 °C / Sealed tube 2: tert.-butylhydroperoxide; sodium iodide / water / 6 h / 20 °C With pyridine, tert.-butylhydroperoxide, iodine, sodium iodide in water Ramanathan, Mani; Kuo, Chun-Kai; Liu, Shiuh-Tzung; Organic and Biomolecular Chemistry; vol. 14; nb. 48; (2016); p.

11446 - 11453 View in Reaxys

O

O

O

N

O

Rx-ID: 36238787 View in Reaxys 23/67 Yield 92 %

Conditions & References With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in acetonitrile, Green chemistry Kotha, Surya Srinivas; Sekar, Govindasamy; Tetrahedron Letters; vol. 56; nb. 46; (2015); p. 6323 - 6326 View in Reaxys

74 %

With oxygen, tetra-(n-butyl)ammonium iodide in ethanol, T= 20 °C , Electrochemical reaction Zhang, Zhenlei; Su, Jihu; Zha, Zhenggen; Wang, Zhiyong; Chemical Communications; vol. 49; nb. 79; (2013); p. 8982 8984 View in Reaxys Reaction Steps: 2 1: acetic acid; copper(I) oxide; oxygen / 120 °C 2: acetic acid; copper(I) oxide; oxygen / 120 °C With copper(I) oxide, oxygen, acetic acid Zhou, Mingxin; Song, Qiuling; Synthesis (Germany); vol. 46; nb. 14; (2014); p. 1853 - 1858; Art.No: SS-2014-C0127-ST View in Reaxys

O

HO

N

O

Rx-ID: 39638828 View in Reaxys 24/67 Yield

Conditions & References Reaction Steps: 2

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

1: tert.-butylhydroperoxide; copper(l) iodide / neat (no solvent) / 5 h / 50 °C / Inert atmosphere 2: copper(l) iodide; oxygen / neat (no solvent) / 16 h / 50 °C With tert.-butylhydroperoxide, copper(l) iodide, oxygen in neat (no solvent) Sharma, Nidhi; Kotha, Surya Srinivas; Lahiri, Nabajit; Sekar, Govindasamy; Synthesis (Germany); vol. 47; nb. 5; (2015); p. 726 - 736; Art.No: SS-2014-T0695-OP View in Reaxys

O O

N

N

O

Rx-ID: 40851256 View in Reaxys 25/67 Yield

Conditions & References

78 %

With di-tert-butyl peroxide, tetra-(n-butyl)ammonium iodide, caesium carbonate, Time= 12h, T= 120 °C Fan, Weizheng; Shi, Dongyang; Feng, Bainian; Tetrahedron Letters; vol. 56; nb. 31; (2015); p. 4638 - 4641 View in Reaxys

H N

HO

O

O

N

O

Rx-ID: 41183800 View in Reaxys 26/67 Yield

Conditions & References Stage 1: With thionyl chloride, triethylamine in dichloromethane, Time= 0.333333h, T= 0 °C , Inert atmosphere Stage 2: in dichloromethane, T= 0 °C , Inert atmosphere Mamillapalli, N. Chary; Sekar, Govindasamy; Advanced Synthesis and Catalysis; vol. 357; nb. 14-15; (2015); p. 3273 - 3283 View in Reaxys

H N

O

HO

O

N

O

Rx-ID: 41441108 View in Reaxys 27/67 Yield 95 %

Conditions & References Typical Experimental procedure for the synthesis of α-keto amides from 2-hydroxy acetopenones General procedure: In a reaction tube IBX (320 mg, 3.0 mmol), 2-hydroxy acetopheneone and piperidine (4 mmol) were dissolved in 3 mL of acetonitrile at room temperature. Reaction mixture was stirred at room temapeature for 4 hours. The completion ofthe reaction was monitored (absence of starting material) by TLC. After completion of the reaction, acetonitrile was removed under reduced pressure.The crude reaction mixture was extracted with ethyl acetate for few times andthe combined ethyl acetate layer was washed with saturated sodium bicarbonate solution. Finally, ethyl acetate layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (petroleum ether:ethyl acetate; 85:15) to give the desired pure tertiary δ-keto amide).

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in acetonitrile, Time= 4h, T= 20 °C , Green chemistry, Reagent/catalyst, Solvent Kotha, Surya Srinivas; Sekar, Govindasamy; Tetrahedron Letters; vol. 56; nb. 46; (2015); p. 6323 - 6326 View in Reaxys 91 %

With pyridine, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, iron(II) acetate in acetonitrile, Time= 3h, T= 60 °C , Schlenk technique Kotha, Surya Srinivas; Chandrasekar, Selvaraj; Sahu, Samrat; Sekar, Govindasamy; European Journal of Organic Chemistry; vol. 2014; nb. 33; (2014); p. 7451 - 7457 View in Reaxys

H N

O

O

HO

N

O

O

Rx-ID: 35466690 View in Reaxys 28/67 Yield

Conditions & References

12 %

With silver (II) carbonate, dipotassium peroxodisulfate in tetrachloromethane, N,N-dimethyl-formamide, Time= 12h, T= 120 °C Zhang, Xiaobin; Yang, Wenchao; Wang, Lei; Organic and Biomolecular Chemistry; vol. 11; nb. 22; (2013); p. 3649 - 3654 View in Reaxys Stage 1: With thionyl chloride, triethylamine in dichloromethane, Time= 0.333333h, T= 0 °C , Inert atmosphere Stage 2: in dichloromethane, T= 0 - 20 °C , Inert atmosphere Mamillapalli, N. Chary; Sekar, Govindasamy; RSC Advances; vol. 4; nb. 105; (2014); p. 61077 - 61085 View in Reaxys

O

H N

O

I

C

N

O

N

O

Rx-ID: 37057378 View in Reaxys 29/67 Yield

Conditions & References With [Bmim][PdI2](PPh3), potassium carbonate in 1,4-dioxane, Time= 5h, T= 90 °C , p= 15001.5Torr , Autoclave, Solvent, Reagent/catalyst Zheng, Shuzhan; Wang, Yan; Zhang, Chunyan; Liu, Jianhua; Xia, Chungu; Applied Organometallic Chemistry; vol. 28; nb. 1; (2014); p. 48 - 53 View in Reaxys

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17/30

2018-08-10 16:28:12

1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

O O

N

N

O

Rx-ID: 38066307 View in Reaxys 30/67 Yield

Conditions & References

60 %

With tert.-butylhydroperoxide, tetra-(n-butyl)ammonium iodide, Time= 18h, T= 80 °C , Sealed tube Du, Bingnan; Jin, Bo; Sun, Peipei; Organic and Biomolecular Chemistry; vol. 12; nb. 26; (2014); p. 4586 - 4589 View in Reaxys

H N

O

O

O

N O

N

O

Rx-ID: 38116754 View in Reaxys 31/67 Yield

Conditions & References

16 %

With copper(I) bromide in dichloromethane, Time= 12h, T= 25 °C , Sealed tube Shao, Ying; Wu, Zhuhong; Miao, Chunbao; Liu, Li; Journal of Organometallic Chemistry; vol. 767; (2014); p. 60 - 64 View in Reaxys

H N

O

O

N O

N

O

Rx-ID: 38204163 View in Reaxys 32/67 Yield 40 %

Conditions & References -α Ketoamides from Aryl Methyl Ketones and DMF; Phenyl-N,N-dimethyl-2-oxoacetamide (3a);10 Typical Procedure General procedure: A Schlenk tube was charged with acetophenone (1a; 60 mg, 0.5 mmol), AcOH (60 mg, 1 mmol), and Cu2O (14.3 mg, 0.1 mmol, 20 molpercent) in DMF (1 mL). The resulting solution was stirred at 120 °C under O2. Upon completion of the reaction [monitored by TLC (eluent:PE–EtOAc, 6:1) and GC], EtOAc (20 mL) was added. The organic layer was washed with sat. aq NaHCO3 (2 × 15 mL) and brine (20 mL). The combined aqueous layers were extracted with EtOAc (2 × 15 mL) and the combined organic layers were dried (Na2SO4). The solvents were removed via rotary evaporator and the residue was purified with flash chromatography [silica gel 200–300 mesh, petroleum ether–EtOAc, 5:1] to give 3a; yield: 57.5 mg (65percent); yellow oil. [CAS Reg. No. 51579-87-4] With copper(I) oxide, oxygen, acetic acid, T= 120 °C Zhou, Mingxin; Song, Qiuling; Synthesis (Germany); vol. 46; nb. 14; (2014); p. 1853 - 1858; Art.No: SS-2014-C0127-ST View in Reaxys

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18/30

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

O

O

HO

N

O

Rx-ID: 38204176 View in Reaxys 33/67 Yield

Conditions & References Reaction Steps: 2 1: acetic acid; copper(I) oxide; oxygen / 120 °C 2: acetic acid; copper(I) oxide; oxygen / 120 °C With copper(I) oxide, oxygen, acetic acid Zhou, Mingxin; Song, Qiuling; Synthesis (Germany); vol. 46; nb. 14; (2014); p. 1853 - 1858; Art.No: SS-2014-C0127-ST View in Reaxys

O O

N

N

O

Rx-ID: 42675456 View in Reaxys 34/67 Yield

Conditions & References

71 %

With [bis(acetoxy)iodo]benzene, sulfuric acid in ethyl acetate, T= 20 °C Liu, Le; Du, Liang; Zhang-Negrerie, Daisy; Du, Yunfei; Zhao, Kang; Organic Letters; vol. 16; nb. 21; (2014); p. 5772 5775 View in Reaxys

H N

O

N

O

Rx-ID: 42675458 View in Reaxys 35/67 Yield

Conditions & References Reaction Steps: 2 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3.5 h / 20 °C 1.2: 20 °C 2.1: [bis(acetoxy)iodo]benzene; sulfuric acid / ethyl acetate / 20 °C With oxalyl dichloride, [bis(acetoxy)iodo]benzene, sulfuric acid, N,N-dimethyl-formamide in dichloromethane, ethyl acetate Liu, Le; Du, Liang; Zhang-Negrerie, Daisy; Du, Yunfei; Zhao, Kang; Organic Letters; vol. 16; nb. 21; (2014); p. 5772 5775 View in Reaxys

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19/30

2018-08-10 16:28:12

1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

O O

N

O

N

O

Rx-ID: 34054655 View in Reaxys 36/67 Yield

Conditions & References

64 %

With tert.-butylhydroperoxide, iodine, benzoic acid in toluene, Time= 12h, T= 80 °C , Sealed tube Zhao, Qiong; Miao, Tao; Zhang, Xiaobin; Zhou, Wei; Wang, Lei; Organic and Biomolecular Chemistry; vol. 11; nb. 11; (2013); p. 1867 - 1873 View in Reaxys

58 %

With tert.-butylhydroperoxide, tetra-(n-butyl)ammonium iodide in water, Time= 16h, T= 100 °C Mai, Wen-Peng; Wang, Hui-Hui; Li, Zhi-Cheng; Yuan, Jin-Wei; Xiao, Yong-Mei; Yang, Liang-Ru; Mao, Pu; Qu, LingBo; Chemical Communications; vol. 48; nb. 81; (2012); p. 10117 - 10119 View in Reaxys

H N

O

O

N

O

O

Rx-ID: 34635029 View in Reaxys 37/67 Yield

Conditions & References

64 %

General procedure for the N-alkylation of azoles using KOtBu as base under NBS-promoted conditions General procedure: 1-phenylbutane-1,3-dione 1a (0.2 mmol, 32.4 mg), 1H-benzo[d][1,2,3]triazole 2a (0.2 mmol, 23.8 mg), Nbromosuccinimide (NBS) (39.2 mg, 1.2 equiv), KOtBu (44.8 mg, 2 equiv) and EtOAc (2 mL) were added to a flask with a magnetic stirring bar. The resulting mixture was stirred for 6 h at 60 oC. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 5/1-2/1 as eluent) to give product 3a and 4a as light yellow and pink solids. The identity and purity of the products was confirmed by 1H and 13C NMR spectroscopic analysis With N-Bromosuccinimide, potassium tert-butylate in ethyl acetate, Time= 6h, T= 60 °C , Green chemistry Chen, Wen-Lin; Li, Ji-Hui; Meng, Xu; Tang, Dong; Guo, Shuai-Bo; Chen, Bao-Hua; Tetrahedron Letters; vol. 54; nb. 4; (2013); p. 295 - 299 View in Reaxys

O

O

H N

O

N

O

Rx-ID: 34777543 View in Reaxys 38/67 Yield 70 %

Conditions & References With tert.-butylhydroperoxide, iodine in ethyl acetate, Time= 8h, T= 80 °C , Green chemistry Zhang, Xiaobin; Wang, Min; Zhang, Yicheng; Wang, Lei; RSC Advances; vol. 3; nb. 5; (2013); p. 1311 - 1316

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

View in Reaxys

O O

O

N HO

N

O

O

Rx-ID: 35284524 View in Reaxys 39/67 Yield

Conditions & References

87 %

With di-tert-butyl peroxide, trimethylpyruvic acid, copper(ll) bromide in toluene, Time= 18h, T= 110 °C Li, Dengke; Wang, Min; Liu, Jie; Zhao, Qiong; Wang, Lei; Chemical Communications; vol. 49; nb. 35; (2013); p. 3640 3642 View in Reaxys

70 %

With di-tert-butyl peroxide, copper diacetate, Time= 3h, T= 110 °C , Schlenk technique, Inert atmosphere Wang, Hua; Guo, Li-Na; Duan, Xin-Hua; Organic and Biomolecular Chemistry; vol. 11; nb. 28; (2013); p. 4573 - 4576 View in Reaxys

O

O

HO

N

N

O

O

Rx-ID: 35466687 View in Reaxys 40/67 Yield

Conditions & References

46 %

With silver (II) carbonate, dipotassium peroxodisulfate in tetrachloromethane, N,N-dimethyl-formamide, Time= 12h, T= 120 °C Zhang, Xiaobin; Yang, Wenchao; Wang, Lei; Organic and Biomolecular Chemistry; vol. 11; nb. 22; (2013); p. 3649 - 3654 View in Reaxys

O

H N O

O

N

O

Rx-ID: 36795710 View in Reaxys 41/67 Yield 75 %

Conditions & References With copper(l) iodide, oxygen in toluene, T= 70 °C , p= 760.051Torr Zhang, Jian; Liu, Yu; Chiba, Shunsuke; Loh, Teck-Peng; Chemical Communications; vol. 49; nb. 97; (2013); p. 11439 11441 View in Reaxys

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

H N

O

O

HO

N

OH

O

Rx-ID: 36795711 View in Reaxys 42/67 Yield

Conditions & References

83 %

With copper(l) iodide, oxygen in toluene, T= 70 °C , p= 760.051Torr Zhang, Jian; Liu, Yu; Chiba, Shunsuke; Loh, Teck-Peng; Chemical Communications; vol. 49; nb. 97; (2013); p. 11439 11441 View in Reaxys

O

H N

O

O

HO

O

N

O

Rx-ID: 36795712 View in Reaxys 43/67 Yield

Conditions & References

99 %, 98 %

With copper(l) iodide, oxygen in toluene, T= 70 °C , p= 760.051Torr Zhang, Jian; Liu, Yu; Chiba, Shunsuke; Loh, Teck-Peng; Chemical Communications; vol. 49; nb. 97; (2013); p. 11439 11441 View in Reaxys

O

H N

O

O

HO

N

O

Rx-ID: 36795715 View in Reaxys 44/67 Yield

Conditions & References

81 %, 76 %

With copper(l) iodide, oxygen in toluene, T= 70 °C , p= 760.051Torr Zhang, Jian; Liu, Yu; Chiba, Shunsuke; Loh, Teck-Peng; Chemical Communications; vol. 49; nb. 97; (2013); p. 11439 11441 View in Reaxys

O

H N

O

O

N

O

Rx-ID: 36795717 View in Reaxys 45/67

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

Yield

Conditions & References

9%

With copper(l) iodide, oxygen in methanol, T= 70 °C , p= 760.051Torr , Sealed tube Zhang, Jian; Liu, Yu; Chiba, Shunsuke; Loh, Teck-Peng; Chemical Communications; vol. 49; nb. 97; (2013); p. 11439 11441 View in Reaxys

O

H N

O

O

HO

N

O

Rx-ID: 36795718 View in Reaxys 46/67 Yield

Conditions & References

88 %, 63 %

With copper(l) iodide, oxygen in toluene, T= 70 °C , p= 760.051Torr , Sealed tube, Reagent/catalyst, Solvent, Temperature Zhang, Jian; Liu, Yu; Chiba, Shunsuke; Loh, Teck-Peng; Chemical Communications; vol. 49; nb. 97; (2013); p. 11439 11441 View in Reaxys

60 %, 62 %

With copper(l) iodide, oxygen in toluene, T= 50 °C , p= 760.051Torr Zhang, Jian; Liu, Yu; Chiba, Shunsuke; Loh, Teck-Peng; Chemical Communications; vol. 49; nb. 97; (2013); p. 11439 11441 View in Reaxys

O

H N

O

O

O

O

N

O

O

O

OH

Rx-ID: 36795720 View in Reaxys 47/67 Yield

Conditions & References

70 %, 36 %

With copper(l) iodide, oxygen in toluene, T= 70 °C , p= 760.051Torr , Sealed tube Zhang, Jian; Liu, Yu; Chiba, Shunsuke; Loh, Teck-Peng; Chemical Communications; vol. 49; nb. 97; (2013); p. 11439 11441 View in Reaxys

O

H N

O

O

HO

N

OH

O

Rx-ID: 36795728 View in Reaxys 48/67 Yield 81 %, 65 %

Conditions & References With copper(l) iodide, oxygen in toluene, T= 70 °C , p= 760.051Torr , Sealed tube

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

Zhang, Jian; Liu, Yu; Chiba, Shunsuke; Loh, Teck-Peng; Chemical Communications; vol. 49; nb. 97; (2013); p. 11439 11441 View in Reaxys

O

O

O

HO

N

O

Rx-ID: 36795742 View in Reaxys 49/67 Yield

Conditions & References Reaction Steps: 2 1: potassium carbonate / water; ethanol; acetone / 1.5 h / 20 °C 2: copper(l) iodide; oxygen / toluene / 70 °C / 760.05 Torr / Sealed tube With copper(l) iodide, oxygen, potassium carbonate in ethanol, water, acetone, toluene Zhang, Jian; Liu, Yu; Chiba, Shunsuke; Loh, Teck-Peng; Chemical Communications; vol. 49; nb. 97; (2013); p. 11439 11441 View in Reaxys

H N

O

O

I

N

O

Rx-ID: 33778949 View in Reaxys 50/67 Yield

Conditions & References

94 %

With tert.-butylhydroperoxide, T= 20 °C Zhang, Xiaobin; Wang, Lei; Green Chemistry; vol. 14; nb. 8; (2012); p. 2141 - 2145 View in Reaxys

H N

O

O

Br Br

N

O

Rx-ID: 28420193 View in Reaxys 51/67 Yield 52 %

Conditions & References in tetrahydrofuran, air Shanmugapriya; Shankar; Satyanarayana; Dahanukar, Vilas H.; Kumar, U. K. Syam; Vembu; Synlett; nb. 19; (2008); p.

2945 - 2950 View in Reaxys

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

O O

N

N

O

Rx-ID: 11258757 View in Reaxys 52/67 Yield

Conditions & References

93 %

With air, tetrabutylammomium bromide, caesium carbonate in N,N-dimethyl-formamide, Time= 6h, T= 120 °C Song, Bingrui; Wang, Siyuan; Sun, Caiyun; Deng, Hongmei; Xu, Bin; Tetrahedron Letters; vol. 48; nb. 51; (2007); p. 8982 8986 View in Reaxys

O O

O

O

N N

N

N

O

Rx-ID: 10282075 View in Reaxys 53/67 Yield

Conditions & References

3.9 %, 0.5 %, 1.4 %

With sodium periodate in methanol, Time= 24h, T= 20 °C Moehrle; Rohn; Westle; Pharmazie; vol. 61; nb. 5; (2006); p. 391 - 399 View in Reaxys

N

O

H N

O

O

N

N Cl

O

Cl

Rx-ID: 9377606 View in Reaxys 54/67 Yield

Conditions & References

18 %, 30 %

With 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile, Time= 48h, T= 80 °C Khlebnikov; Novikov; Kusei; Kopf; Kostikov; Russian Journal of Organic Chemistry; vol. 39; nb. 4; (2003); p. 559 - 573 View in Reaxys

-1 F (v4)

H N

F

C

B FF

O

O I+

N

O

Rx-ID: 8799660 View in Reaxys 55/67

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

Yield

Conditions & References

85 %

With bis-triphenylphosphine-palladium(II) chloride, copper(l) iodide in N,N-dimethyl-formamide, T= 20 °C Zhou, Tao; Chen, Zhen-Chu; Journal of Chemical Research - Part S; nb. 3; (2001); p. 116 - 117 View in Reaxys

O

O

O

H N

O O O

N O

N

O

N

Rx-ID: 5313436 View in Reaxys 56/67 Yield

Conditions & References

13 %, 38 %

in dichloromethane, Time= 0.5h, T= -78 °C , Substitution Wasserman, Harry H.; Lee, Kieseung; Xia, Mingde; Tetrahedron Letters; vol. 41; nb. 15; (2000); p. 2511 - 2514 View in Reaxys

O O P

N

O

O N

Rx-ID: 16071993 View in Reaxys 57/67 Yield

Conditions & References Reaction Steps: 2 1: O3; 4 Angstroem molecular sieves / CH2Cl2 / -78 °C 2: 13 percent / CH2Cl2 / 0.5 h / -78 °C With 4 A molecular sieve, ozone in dichloromethane, 1: Oxidation / 2: Substitution Wasserman, Harry H.; Lee, Kieseung; Xia, Mingde; Tetrahedron Letters; vol. 41; nb. 15; (2000); p. 2511 - 2514 View in Reaxys

O

H N

O

O

O

N

O

Rx-ID: 1480790 View in Reaxys 58/67 Yield 79 %

Conditions & References Time= 42h, T= 90 - 95 °C Imai, Nobuyuki; Achiwa, Kazuo; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 7; (1987); p. 2646 - 2655 View in Reaxys Axten, Jeffrey M.; Krim, Lori; Kung, Hank F.; Winkler, Jeffrey D.; Journal of Organic Chemistry; vol. 63; nb. 26; (1998); p.

9628 - 9629

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

View in Reaxys

N O

Li

O N

O

O

O

N

O

O

Rx-ID: 1987273 View in Reaxys 59/67 Yield

Conditions & References Ambient temperature Mueller-Westerhoff, Ulrich T.; Zhou, Ming; Tetrahedron Letters; vol. 34; nb. 4; (1992); p. 571 - 574 View in Reaxys

H N

O

O

O

O

N

O

HO

Rx-ID: 1482069 View in Reaxys 60/67 Yield

Conditions & References

82 % Chromat., 17 % Chromat.

With oxygen, <<Fe(salen)>2O> in acetonitrile, Time= 2h, T= 60 °C , pyridine

82 % Chromat., 17 % Chromat.

With oxygen, <<Fe(salen)>2O> in acetonitrile, Time= 2h, T= 60 °C , pyridine; in the presence of BHT; 20 deg C; further arylglyoxals, further secondary amines, Product distribution

Murata, Satoru; Suzuki, Kaoru; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 2; (1990); p. 361 - 365 View in Reaxys

Murata, Satoru; Suzuki, Kaoru; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 2; (1990); p. 361 - 365 View in Reaxys

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

O O

O

O

N

N

N

HO

O

Rx-ID: 1801500 View in Reaxys 61/67 Yield

Conditions & References

20 % Chromat., 11 % Chromat., 36 % Chromat.

With diphenyl sulfide, oxygen, <<Fe(salen)>2O> in acetonitrile, Time= 2h, T= 20 °C

16 % Chromat., 7 % Chromat., 33 % Chromat.

With oxygen, <<Fe(salen)>2O> in acetonitrile, Time= 2h, T= 20 °C , with and without 2-mercaptoethanol, benzthiol, diphenyl sulphide; air; other solvents: pyridine, pyridine, water; other catalysts; other N,N-(dialkyl)acylmethylamines, Product distribution

Murata, Satoru; Suzuki, Kaoru; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 2; (1990); p. 361 - 365 View in Reaxys

Murata, Satoru; Suzuki, Kaoru; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 2; (1990); p. 361 - 365 View in Reaxys

O

O HO

S S

N

N

OH

O

Rx-ID: 1801501 View in Reaxys 62/67 Yield

Conditions & References With oxygen, 2-hydroxyethanethiol, <<Fe(salen)>2O> in acetonitrile, Time= 2h, T= 20 °C , Yield given. Yields of byproduct given Murata, Satoru; Suzuki, Kaoru; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 2; (1990); p. 361 - 365 View in Reaxys

O

O

N

N

O

HO

O

Rx-ID: 1801506 View in Reaxys 63/67 Yield 70 % Chromat., 10 % Chromat.

Conditions & References With air, 2-hydroxyethanethiol, <<Fe(salen)>2O> in acetonitrile, Time= 2h, T= 20 °C , oxygen, sodium sulphide Murata, Satoru; Suzuki, Kaoru; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 2; (1990); p. 361 - 365 View in Reaxys

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

O

O

N

N

O

O

N

O

S

HO

Rx-ID: 1801507 View in Reaxys 64/67 Yield

Conditions & References

3 % ChroWith sodium sulfide, air, <<Fe(salen)>2O> in pyridine, water, Time= 2h, T= 20 °C , acetonitrile, water; oxygen; other catalysts; mat., 75 % other cond.: sulphur; in absence of catalyst; 5h; 60 deg C; further N,N-(dialkyl)acylmethylamines, Product distribution Chromat., 4 % Chromat. Murata, Satoru; Suzuki, Kaoru; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 2; (1990); p. 361 - 365 View in Reaxys 4 % ChroWith sodium sulfide, air, <<Fe(salen)>2O> in pyridine, water, Time= 2h, T= 20 °C mat., 75 % Chromat., 3 Murata, Satoru; Suzuki, Kaoru; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Perkin Transac% Chromat. tions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 2; (1990); p. 361 - 365 View in Reaxys

H N

O Br

C

O

O

N

N

O

Rx-ID: 1481452 View in Reaxys 65/67 Yield

Conditions & References

21 % Chromat., 79 % Chromat.

With PdCl2(PMePh2)2 in neat (no solvent), Time= 24h, T= 100 °C , p= 7600Torr Ozawa, Fumiyuki; Soyama, Hidehiko; Yanagihara, Hisayoshi; Aoyama, Issei; Takino, Hiroaki; et al.; Journal of the American Chemical Society; vol. 107; nb. 11; (1985); p. 3235 - 3245 View in Reaxys With PdCl2(PMePh2)2, Time= 64h, T= 100 °C , p= 7600Torr , Yield given. Yields of byproduct given Ozawa, Fumiyuki; Soyama, Hidehiko; Yamamoto, Takakazu; Yamamoto, Akio; Tetrahedron Letters; vol. 23; nb. 33; (1982); p. 3383 - 3386 View in Reaxys

H N

O

I

C

N

O

O

O

N

N

O

O N

Rx-ID: 1481679 View in Reaxys 66/67 Yield

Conditions & References With trans-{PdMe2(PMePh2)2} in neat (no solvent), Time= 2h, p= 15200Torr , Ambient temperature, Product distribution, Mechanism

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1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione [C13H15NO2]

Ozawa, Fumiyuki; Soyama, Hidehiko; Yanagihara, Hisayoshi; Aoyama, Issei; Takino, Hiroaki; et al.; Journal of the American Chemical Society; vol. 107; nb. 11; (1985); p. 3235 - 3245 View in Reaxys

H N

O C

O

O

N

N

O

Rx-ID: 1482974 View in Reaxys 67/67 Yield

Conditions & References With trans-PdPh(I)(PMePh2)2 in neat (no solvent), Time= 0.166667h, p= 15200Torr , Ambient temperature, other reagent, other reaction time, Product distribution, Mechanism Ozawa, Fumiyuki; Soyama, Hidehiko; Yanagihara, Hisayoshi; Aoyama, Issei; Takino, Hiroaki; et al.; Journal of the American Chemical Society; vol. 107; nb. 11; (1985); p. 3235 - 3245 View in Reaxys

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