2-Hydroxy-2-phenyl-1-(piperidin-1-yl)ethan-1-one [C13H17NO2]

2-Hydroxy-2-phenyl-1-(piperidin-1-yl)ethan-1-one [C13H17NO2]

Query Query

O

1. Query

HO

Results

Date

14 reactions in Reaxys

2018-08-10 15h:59m:32s (UTC)

N

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='102423-80-3') AND (IDE.INCHI='VBZMYBKKVZQZPTUHFFFAOYSA-N') NOT (RX.RXRN=12301))

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2-Hydroxy-2-phenyl-1-(piperidin-1-yl)ethan-1-one [C13H17NO2]

O

O

O

O HO O

N

O

Si O N

N

O

Rx-ID: 41826187 View in Reaxys 1/14 Yield

Conditions & References in tetrahydrofuran, Time= 0.5h, T= -70 °C , Inert atmosphere Sun, Zhao; Liu, Hui; Zeng, Yong-Ming; Lu, Chong-Dao; Xu, Yan-Jun; Organic Letters; vol. 18; nb. 3; (2016); p. 620 - 623 View in Reaxys

O O HO

N

O

N

Rx-ID: 1736270 View in Reaxys 2/14 Yield

Conditions & References

98 %

Stage 1: With tetrabutyl ammonium fluoride, HSiPh3 in tetrahydrofuran, Time= 8h, T= 20 °C , Inert atmosphere Stage 2: With water, sodium hydroxide in tetrahydrofuran, Time= 0.166667h, chemoselective reaction Mamillapalli, N. Chary; Sekar, Govindasamy; RSC Advances; vol. 4; nb. 105; (2014); p. 61077 - 61085 View in Reaxys

86 %

With potassium tetrachloropalladate(II) in tetrahydrofuran, Time= 18h, T= 60 °C , Inert atmosphere, chemoselective reaction Mamillapalli, N. Chary; Sekar, Govindasamy; Advanced Synthesis and Catalysis; vol. 357; nb. 14-15; (2015); p. 3273 - 3283 View in Reaxys

60 %

With zinc(II) chloride, zinc in ethanol, Time= 1h, Heating Toda, Fumio; Tanaka, Koichi; Tange, Hiroshi; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1989); p. 1555 - 1556 View in Reaxys

H N O HO N

Rx-ID: 39871994 View in Reaxys 3/14 Yield

Conditions & References Reaction Steps: 2

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2-Hydroxy-2-phenyl-1-(piperidin-1-yl)ethan-1-one [C13H17NO2]

1.1: triethylamine; thionyl chloride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride; HSiPh3 / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 2.2: 0.17 h With thionyl chloride, tetrabutyl ammonium fluoride, triethylamine, HSiPh3 in tetrahydrofuran, dichloromethane Mamillapalli, N. Chary; Sekar, Govindasamy; RSC Advances; vol. 4; nb. 105; (2014); p. 61077 - 61085 View in Reaxys Reaction Steps: 2 1.1: thionyl chloride; triethylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: potassium tetrachloropalladate(II) / tetrahydrofuran / 18 h / 60 °C / Inert atmosphere With thionyl chloride, potassium tetrachloropalladate(II), triethylamine in tetrahydrofuran, dichloromethane Mamillapalli, N. Chary; Sekar, Govindasamy; Advanced Synthesis and Catalysis; vol. 357; nb. 14-15; (2015); p. 3273 - 3283 View in Reaxys

HO

O HO

O

N

Rx-ID: 41183788 View in Reaxys 4/14 Yield

Conditions & References Reaction Steps: 2 1.1: thionyl chloride; triethylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: potassium tetrachloropalladate(II) / tetrahydrofuran / 18 h / 60 °C / Inert atmosphere With thionyl chloride, potassium tetrachloropalladate(II), triethylamine in tetrahydrofuran, dichloromethane Mamillapalli, N. Chary; Sekar, Govindasamy; Advanced Synthesis and Catalysis; vol. 357; nb. 14-15; (2015); p. 3273 - 3283 View in Reaxys

O O HO

HO

N

O

Rx-ID: 39871962 View in Reaxys 5/14 Yield

Conditions & References Reaction Steps: 2 1.1: triethylamine; thionyl chloride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride; HSiPh3 / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 2.2: 0.17 h With thionyl chloride, tetrabutyl ammonium fluoride, triethylamine, HSiPh3 in tetrahydrofuran, dichloromethane Mamillapalli, N. Chary; Sekar, Govindasamy; RSC Advances; vol. 4; nb. 105; (2014); p. 61077 - 61085

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2-Hydroxy-2-phenyl-1-(piperidin-1-yl)ethan-1-one [C13H17NO2]

View in Reaxys

O

O O HO

N

O

N

Rx-ID: 4726123 View in Reaxys 6/14 Yield

Conditions & References With sodium hydroxide, Ambient temperature Freer, Andrew A.; Isaacs, Neil W.; Kirby, Gordon W.; Snedden, Peter; Tierney, Sean G. T.; Journal of Chemical Research, Miniprint; nb. 2; (1996); p. 601 - 621 View in Reaxys

H N

2-<2,6-dihydroxy-3,5-dimethyl-phenoxy>-3,5-dinitro-benzophenone

O HO N

Rx-ID: 17194959 View in Reaxys 7/14 Yield

Conditions & References Reaction Steps: 2 1: CHCl3 2: ethanolic NaOH / Ambient temperature With sodium hydroxide in chloroform Freer, Andrew A.; Isaacs, Neil W.; Kirby, Gordon W.; Snedden, Peter; Tierney, Sean G. T.; Journal of Chemical Research, Miniprint; nb. 2; (1996); p. 601 - 621 View in Reaxys

O O O HO

HO N

O

Rx-ID: 17202332 View in Reaxys 8/14 Yield

Conditions & References Reaction Steps: 3 1: thionyl chloride / Heating 2: CHCl3 3: ethanolic NaOH / Ambient temperature

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2-Hydroxy-2-phenyl-1-(piperidin-1-yl)ethan-1-one [C13H17NO2]

With sodium hydroxide, thionyl chloride in chloroform Freer, Andrew A.; Isaacs, Neil W.; Kirby, Gordon W.; Snedden, Peter; Tierney, Sean G. T.; Journal of Chemical Research, Miniprint; nb. 2; (1996); p. 601 - 621 View in Reaxys

HO O HO

HO

N

O

Rx-ID: 17210428 View in Reaxys 9/14 Yield

Conditions & References Reaction Steps: 4 1: 0.5 h / Ambient temperature 2: thionyl chloride / Heating 3: CHCl3 4: ethanolic NaOH / Ambient temperature With sodium hydroxide, thionyl chloride in chloroform Freer, Andrew A.; Isaacs, Neil W.; Kirby, Gordon W.; Snedden, Peter; Tierney, Sean G. T.; Journal of Chemical Research, Miniprint; nb. 2; (1996); p. 601 - 621 View in Reaxys

O O O HO

Cl N

O

Rx-ID: 17239105 View in Reaxys 10/14 Yield

Conditions & References Reaction Steps: 2 1: CHCl3 2: ethanolic NaOH / Ambient temperature With sodium hydroxide in chloroform Freer, Andrew A.; Isaacs, Neil W.; Kirby, Gordon W.; Snedden, Peter; Tierney, Sean G. T.; Journal of Chemical Research, Miniprint; nb. 2; (1996); p. 601 - 621 View in Reaxys

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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2-Hydroxy-2-phenyl-1-(piperidin-1-yl)ethan-1-one [C13H17NO2]

Cl

O H

N

O HO O

N

Rx-ID: 2164643 View in Reaxys 11/14 Yield

Conditions & References Yield given. Multistep reaction Hiiro, Tomoki; Mogami, Toshiaki; Kambe, Nobuaki; Fujiwara, Shin-Ichi; Sonoda, Noboru; Synthetic Communications; vol. 20; nb. 5; (1990); p. 703 - 711 View in Reaxys

OH

H N O O HO

O N

Rx-ID: 1482342 View in Reaxys 12/14 Yield

Conditions & References

100 %

in acetonitrile, Time= 72h, T= 35 °C , p= 8000Torr Matsumoto, Kiyoshi; Hashimoto, Shiro; Otani, Shinichi; Angewandte Chemie; vol. 98; nb. 6; (1986); p. 569 - 570 View in Reaxys

63 %

in acetonitrile, Time= 72h, T= 35 °C , p= 6000480Torr Matsumoto, Kiyoshi; Hashimoto, Shiro; Uchida, Takane; Okamoto, Tadashi; Otani, Shinichi; Chemische Berichte; vol.

122; (1989); p. 1357 - 1364 View in Reaxys

H N

O

O HO

O O

N

Rx-ID: 3824212 View in Reaxys 13/14 Yield 84 %

Conditions & References in tetrahydrofuran, Time= 48h, Ambient temperature Wanner; Schuenemann; Archiv der Pharmazie; vol. 320; nb. 11; (1987); p. 1161 - 1167 View in Reaxys

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2-Hydroxy-2-phenyl-1-(piperidin-1-yl)ethan-1-one [C13H17NO2]

OH

H N O

O HO O

N

Rx-ID: 14035 View in Reaxys 14/14 Yield

Conditions & References T= 120 °C McKenzie; Martin; Rule; Journal of the Chemical Society; vol. 105; (1914); p. 1586 View in Reaxys

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