1-(2,5-dimethoxyphenyl)propan-2-amine (2,5-DMA) [CAS 2801-68-5; InChIKey LATVFYDIBMDBSY-UHFFF

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Date

38 reactions in Reaxys

2016-04-20 08h:14m:35s (EST)

O

1. Query

NH 2

O

Search as: As drawn

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H

O

N

N

N

O

H 2N

O

O

Rx-ID: 9422259 View in Reaxys 1/38 Yield

Conditions & References

100 %

With hydrogen, palladium on activated charcoal in methanol, Time= 12h, p= 2068.59 - 2327.17Torr Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy; Tetrahedron Asymmetry; vol. 14; nb. 15; (2003); p. 2119 - 2125 View in Reaxys

H

O

N

N

O

H 2N

N

O

O

Rx-ID: 28792623 View in Reaxys 2/38 Yield

Conditions & References 1 :A solution of (R)-I -(2,5- dimethoxy-phenyl)-propan-2-ol (1.2 g, 5.4 mmol) and DIEA (1.88 mL, 10.8 mmol) in 20 mL of anhydrous DCM was cooled to -10 °C. Then MsCl (742 mg, 6.48 mmol) was carefully added and the mixture was warmed to RT and stirred for 30 min. Then 10 mL of sat. NaHCO3 was added and the mixture was extracted with DCM (2x20 mL). The extract was dried over Na2SO4 and evaporated to give crude oil of mesylate. This oil was dissolved in 5 mL of anh. DMF. Then NaN3 (702 mg, 10.8 mmol) was added and the mixture was heated at 80 °C for 2 h. Then 30 mL of water added and extracted with 20 mL of EtOAc/hexane 1 : 1 mixture. The extract was dried over Na2SO4 and evaporated to give crude oil of azide, which was dissolved in 50 mL of EtOAc, then Pd/C (150 mg of 10percent Pd) was added and the mixture was hydrogenated under hydrogen balloon for 3 h. The catalyst was removed by filtration through celite, the mixture was evaporated and the crude residue was used directly in the next step.

With hydrogen, palladium 10 on activated carbon in ethyl acetate, Time= 3h Patent; CHEMBRIDGE CORPORATION; WO2009/117097; (2009); (A1) English View in Reaxys O

O

H 2N

O O

N O

O

Rx-ID: 965492 View in Reaxys 3/38 Yield

Conditions & References With lithium aluminium tetrahydride Bailey,K. et al.; Canadian Journal of Chemistry; vol. 49; (1971); p. 3143 - 3151 View in Reaxys With lithium aluminium tetrahydride in diethyl ether, Heating Coutts; Malicky; Canadian Journal of Chemistry; vol. 51; nb. 9; (1973); p. 1402 - 1409 View in Reaxys 13 : Example 13 Example 13 Preparation of 1-(2,5-dimethoxyphenyl) propan-2-amine 12 Lithium aluminum hydride (7.15g, 0.19mol) was added portion-wise to anhydrous tetrahydrofuran (300ml) and then (E)-1,4-dimethoxy-2-(2-nitroprop-1-en-1-yl) benzene 11 (14g, 0.063mol) dissolved in anhydrous tetrahydrofuran (200ml) was added drop-wise.

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The reaction mixture was refluxed overnight.

To quench the reaction mixture, water (7ml) followed by 1 M sodium hydroxide (7ml) and then water (21 ml) were added slowly with cooling.

The resulting mixture was stirred at room temperature until the formation of white precipitate then filtered on celite plug and washed with diethylether.

The solvent was removed under vacuo to give the 1-(2,5-dimethoxyphenyl) propan-2-amine (12.31g) 12 crude as yellow oil.

With sodium hydroxide in tetrahydrofuran, water Patent; Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip; EP2835648; (2015); (A1) English View in Reaxys O

O O N

H 2N

E

O

O

O

Rx-ID: 39269995 View in Reaxys 4/38 Yield

Conditions & References 13 : Preparation of 1-(2,5-dimethoxyphenyl) propan-2-amine 12 Example 13 Preparation of 1-(2,5-dimethoxyphenyl) propan-2-amine 12 Lithium aluminum hydride (7.15 g, 0.19 mol) was added portion-wise to anhydrous tetrahydrofuran (300 ml) and then (E)-1,4-dimethoxy-2-(2-nitroprop-1-en-1-yl)benzene 11 (14 g, 0.063 mol) dissolved in anhydrous tetrahydrofuran (200 ml) was added drop-wise.

The reaction mixture was refluxed overnight.

To quench the reaction mixture, water (7 ml) followed by 1M sodium hydroxide (7 ml) and then water (21 ml) were added slowly with cooling.

The resulting mixture was stirred at room temperature until the formation of white precipitate then filtered on celite plug and washed with diethylether.

The solvent was removed under vacuo to give the 1-(2,5-dimethoxyphenyl) propan-2-amine (12.31 g) 12 crude as yellow oil.

With sodium hydroxide in tetrahydrofuran, water Patent; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip; US2015/38366; (2015); (A1) English View in Reaxys

O

O H 2N

N

S S

O

HN

O

O

O

Rx-ID: 5121838 View in Reaxys 5/38 Yield 91 %

Conditions & References With thiophenol, N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide, Ambient temperature Wuts, Peter G. M.; Gu, Rui Lin; Northuis, Jill M.; Thomas, Collette L.; Tetrahedron Letters; vol. 39; nb. 50; (1998); p. 9155 - 9156 View in Reaxys

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H

O H

O

H 2N

NH

Cl

H

H

O

O

Rx-ID: 4330799 View in Reaxys 6/38 Yield

Conditions & References With hydrogen, palladium on activated charcoal in methanol, water Nichols; Barfknecht; Rusterholz; Benington; Morin; Journal of medicinal chemistry; vol. 16; nb. 5; (1973); p. 480 - 483 View in Reaxys

H

O H

O

H 2N

NH

Cl

H

H

O

O

Rx-ID: 4330800 View in Reaxys 7/38 Yield

Conditions & References With hydrogen, palladium on activated charcoal in methanol, water Nichols; Barfknecht; Rusterholz; Benington; Morin; Journal of medicinal chemistry; vol. 16; nb. 5; (1973); p. 480 - 483 View in Reaxys

O O

H 2N O S O

O

O

O

Rx-ID: 5325468 View in Reaxys 8/38 Yield

Conditions & References

90 %

With ammonia, Time= 8h, T= 50 - 60 °C , Substitution Yutilov; Malyutina; Shcherbina; Kirillova; Russian Journal of Applied Chemistry; vol. 72; nb. 10; (1999); p. 1787 1792 View in Reaxys

O

O O

H 2N Cl

N H 2N

H

O O

O

Rx-ID: 19076227 View in Reaxys 9/38 Yield

Conditions & References Reaction Steps: 5 1: 81 percent / 3 h / Ambient temperature 2: 82 percent / H2 / Pd/C / ethanol / 2 h / Ambient temperature 3: 1.) NaNO2, HCl / 1.) 0-5 deg C, 30 min, 2.) <5 deg C, 30 min 4: NaI / acetonitrile / 1.) 0 deg C, 30 min, 2.) room temperature, 20 h 5: 65 percent / 15percent NaOH / 14 h / Ambient temperature With hydrogenchloride, sodium hydroxide, hydrogen, sodium iodide, sodium nitrite, palladium on activated charcoal in ethanol, acetonitrile

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Glennon, Richard A.; Seggel, Mark R.; Soine, William H.; Herrick-Davis, Katherine; Lyon, Robert A.; Titeler, Milt; Journal of Medicinal Chemistry; vol. 31; nb. 1; (1988); p. 5 - 7 View in Reaxys

F

F O

F

O

HN

H 2N

O

Cl

N O

O

H

O

O

Rx-ID: 19095120 View in Reaxys 10/38 Yield

Conditions & References Reaction Steps: 4 1: 82 percent / H2 / Pd/C / ethanol / 2 h / Ambient temperature 2: 1.) NaNO2, HCl / 1.) 0-5 deg C, 30 min, 2.) <5 deg C, 30 min 3: NaI / acetonitrile / 1.) 0 deg C, 30 min, 2.) room temperature, 20 h 4: 65 percent / 15percent NaOH / 14 h / Ambient temperature With hydrogenchloride, sodium hydroxide, hydrogen, sodium iodide, sodium nitrite, palladium on activated charcoal in ethanol, acetonitrile Glennon, Richard A.; Seggel, Mark R.; Soine, William H.; Herrick-Davis, Katherine; Lyon, Robert A.; Titeler, Milt; Journal of Medicinal Chemistry; vol. 31; nb. 1; (1988); p. 5 - 7 View in Reaxys O

O

O

O

H 2N

O

Rx-ID: 21983487 View in Reaxys 11/38 Yield

Conditions & References Reaction Steps: 4 1: piperidine / Hydrierung des Reaktionsprodukts, Behandlung des erhaltenen Esters mit Methyljodid und Natriumaethylat und anschliessend Hydrolyse 2: 150 °C 3: ammonia / 220 - 230 °C 4: dioxane; aqueous sodium hypochlorite With piperidine, 1,4-dioxane, sodium hypochlorite, ammonia Baltzly; Buck; Journal of the American Chemical Society; vol. 62; (1940); p. 164,166; Journal of the American Chemical Society; vol. 64; (1942); p. 3040 View in Reaxys Reaction Steps: 2 1: NH4OAc / acetic acid 2: LiAlH4 / diethyl ether / Heating With lithium aluminium tetrahydride, ammonium acetate in diethyl ether, acetic acid Coutts; Malicky; Canadian Journal of Chemistry; vol. 51; nb. 9; (1973); p. 1402 - 1409 View in Reaxys Reaction Steps: 2 1: ammonium acetate / dichloromethane; hexane 2: sodium hydroxide / tetrahydrofuran; water With ammonium acetate, sodium hydroxide in tetrahydrofuran, hexane, dichloromethane, water Patent; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip; US2015/38366; (2015); (A1) English View in Reaxys

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5/14

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F

F

O

F

O

HN

H 2N

O

Cl

H

O

I O

Rx-ID: 2777648 View in Reaxys 12/38 Yield

Conditions & References

65 %

With sodium hydroxide, Time= 14h, Ambient temperature Glennon, Richard A.; Seggel, Mark R.; Soine, William H.; Herrick-Davis, Katherine; Lyon, Robert A.; Titeler, Milt; Journal of Medicinal Chemistry; vol. 31; nb. 1; (1988); p. 5 - 7 View in Reaxys

H

O

Br

H 2N O

O

O

Rx-ID: 14080087 View in Reaxys 13/38 Yield

Conditions & References Reaction Steps: 4 1.1: n-BuLi / tetrahydrofuran; pentane / 0.17 h / -72 °C 1.2: 67 percent / BF3*Et2O / tetrahydrofuran; pentane / 0.42 h 2.1: 57 percent / pyridine / 72 h 3.1: 96 percent / NaN3 / dimethylformamide / 120 h 4.1: 100 percent / H2 / Pd/C / methanol / 12 h / 2068.59 - 2327.17 Torr With pyridine, n-butyllithium, sodium azide, hydrogen, palladium on activated charcoal in tetrahydrofuran, methanol, N,N-dimethyl-formamide, pentane Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy; Tetrahedron Asymmetry; vol. 14; nb. 15; (2003); p. 2119 - 2125 View in Reaxys

H

O HO

O

H 2N

O

O

Rx-ID: 14089256 View in Reaxys 14/38 Yield

Conditions & References Reaction Steps: 3 1: 57 percent / pyridine / 72 h 2: 96 percent / NaN3 / dimethylformamide / 120 h 3: 100 percent / H2 / Pd/C / methanol / 12 h / 2068.59 - 2327.17 Torr With pyridine, sodium azide, hydrogen, palladium on activated charcoal in methanol, N,N-dimethyl-formamide Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy; Tetrahedron Asymmetry; vol. 14; nb. 15; (2003); p. 2119 - 2125 View in Reaxys

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H O

O

H 2N

O S O

O

O

O

Rx-ID: 14103706 View in Reaxys 15/38 Yield

Conditions & References Reaction Steps: 2 1: 96 percent / NaN3 / dimethylformamide / 120 h 2: 100 percent / H2 / Pd/C / methanol / 12 h / 2068.59 - 2327.17 Torr With sodium azide, hydrogen, palladium on activated charcoal in methanol, N,N-dimethyl-formamide Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy; Tetrahedron Asymmetry; vol. 14; nb. 15; (2003); p. 2119 - 2125 View in Reaxys O H 2N

O H 2N

O O

O

Rx-ID: 482431 View in Reaxys 16/38 Yield

Conditions & References With 1,4-dioxane, sodium hypochlorite Baltzly; Buck; Journal of the American Chemical Society; vol. 62; (1940); p. 164,166; Journal of the American Chemical Society; vol. 64; (1942); p. 3040 View in Reaxys 2H

O

HO

2

H

2H

OH

NH 2 2H 2H

O 2H

Rx-ID: 11382612 View in Reaxys 17/38 Yield

Conditions & References Reaction Steps: 4 1.1: KOH / tetrabutylammonium bromide / 20 °C 1.2: 98 percent / 72 h / 40 - 45 °C 2.1: 73 percent / titanium tetrachloride / CH2Cl2 / 0.25 h / 20 °C 3.1: 86 percent / ammonium acetate; acetic acid / 3 h / Heating 4.1: lithium aluminum hydride / diethyl ether / 20 h / Heating With ammonium acetate, potassium hydroxide, lithium aluminium tetrahydride, titanium tetrachloride, acetic acid, tetrabutylammomium bromide in diethyl ether, dichloromethane Xu, Ya-Zhu; Lin, Huei-Ru; Lua, Chang-Ahai; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 2; (2007); p. 493 - 502 View in Reaxys

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7/14

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F

F

O

F

O

HN

H 2N

O

Cl

H

O

NH 2 O

Rx-ID: 19093210 View in Reaxys 18/38 Yield

Conditions & References Reaction Steps: 3 1: 1.) NaNO2, HCl / 1.) 0-5 deg C, 30 min, 2.) <5 deg C, 30 min 2: NaI / acetonitrile / 1.) 0 deg C, 30 min, 2.) room temperature, 20 h 3: 65 percent / 15percent NaOH / 14 h / Ambient temperature With hydrogenchloride, sodium hydroxide, sodium iodide, sodium nitrite in acetonitrile Glennon, Richard A.; Seggel, Mark R.; Soine, William H.; Herrick-Davis, Katherine; Lyon, Robert A.; Titeler, Milt; Journal of Medicinal Chemistry; vol. 31; nb. 1; (1988); p. 5 - 7 View in Reaxys

N O

N

O

N

H 2N Cl

H

O

O

HN F O

F F

Rx-ID: 19096096 View in Reaxys 19/38 Yield

Conditions & References Reaction Steps: 2 1: NaI / acetonitrile / 1.) 0 deg C, 30 min, 2.) room temperature, 20 h 2: 65 percent / 15percent NaOH / 14 h / Ambient temperature With sodium hydroxide, sodium iodide in acetonitrile Glennon, Richard A.; Seggel, Mark R.; Soine, William H.; Herrick-Davis, Katherine; Lyon, Robert A.; Titeler, Milt; Journal of Medicinal Chemistry; vol. 31; nb. 1; (1988); p. 5 - 7 View in Reaxys O

O

H 2N

O O

HO

O

Rx-ID: 21981775 View in Reaxys 20/38 Yield

Conditions & References Reaction Steps: 2 1: ammonia / 220 - 230 °C 2: dioxane; aqueous sodium hypochlorite With 1,4-dioxane, sodium hypochlorite, ammonia Baltzly; Buck; Journal of the American Chemical Society; vol. 62; (1940); p. 164,166; Journal of the American Chemical Society; vol. 64; (1942); p. 3040 View in Reaxys

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OH

O

O

H 2N

O O OH

O O

Rx-ID: 21982002 View in Reaxys 21/38 Yield

Conditions & References Reaction Steps: 3 1: 150 °C 2: ammonia / 220 - 230 °C 3: dioxane; aqueous sodium hypochlorite With 1,4-dioxane, sodium hypochlorite, ammonia Baltzly; Buck; Journal of the American Chemical Society; vol. 62; (1940); p. 164,166; Journal of the American Chemical Society; vol. 64; (1942); p. 3040 View in Reaxys

O

O O

H 2N

S O

O O

O

Rx-ID: 5345628 View in Reaxys 22/38 Yield

Conditions & References

70 %

With ammonia, Substitution Yutilov; Malyutina; Shcherbina; Kirillova; Russian Journal of Applied Chemistry; vol. 72; nb. 10; (1999); p. 1787 1792 View in Reaxys O O

N O H 2N

O O S O

O

O

O

Rx-ID: 5347906 View in Reaxys 23/38 Yield 65 %

Conditions & References With ammonia, Substitution Yutilov; Malyutina; Shcherbina; Kirillova; Russian Journal of Applied Chemistry; vol. 72; nb. 10; (1999); p. 1787 1792 View in Reaxys O H 2N

O

O

2-hydroxy-isophthalic acid-chloride methyl ester O

Rx-ID: 16015073 View in Reaxys 24/38 Yield

Conditions & References Reaction Steps: 3 1.1: n-BuLi / diethyl ether / 20 °C 1.2: 87 percent / diethyl ether / 20 °C 2.1: 97 percent / pyridine / 55 °C 3.1: 90 percent / liq. NH3 / 8 h / 50 - 60 °C

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With pyridine, n-butyllithium, ammonia in diethyl ether, 1.1: Metallation / 1.2: Addition / 2.1: Tosylation / 3.1: Substitution Yutilov; Malyutina; Shcherbina; Kirillova; Russian Journal of Applied Chemistry; vol. 72; nb. 10; (1999); p. 1787 1792 View in Reaxys Reaction Steps: 3 1.1: n-BuLi / diethyl ether / 20 °C 1.2: 87 percent / diethyl ether / 20 °C 2.1: 97.2 percent / pyridine / 20 h / 0 - 5 °C 3.1: 70 percent / liq. NH3 With pyridine, n-butyllithium, ammonia in diethyl ether, 1.1: Metallation / 1.2: Addition / 2.1: Substitution / 3.1: Substitution Yutilov; Malyutina; Shcherbina; Kirillova; Russian Journal of Applied Chemistry; vol. 72; nb. 10; (1999); p. 1787 1792 View in Reaxys Reaction Steps: 3 1.1: n-BuLi / diethyl ether / 20 °C 1.2: 87 percent / diethyl ether / 20 °C 2.1: 87 percent / pyridine 3.1: 65 percent / liq. NH3 With pyridine, n-butyllithium, ammonia in diethyl ether, 1.1: Metallation / 1.2: Addition / 2.1: Substitution / 3.1: Substitution Yutilov; Malyutina; Shcherbina; Kirillova; Russian Journal of Applied Chemistry; vol. 72; nb. 10; (1999); p. 1787 1792 View in Reaxys 2H

2H

2H 2H

O

O

N 2H 2H

O

2

H

2H

O

NH 2 2H

O

2H

2H

O 2H

Rx-ID: 11154053 View in Reaxys 25/38 Yield

Conditions & References With lithium aluminium tetrahydride in diethyl ether, Time= 20h, Heating Xu, Ya-Zhu; Lin, Huei-Ru; Lua, Chang-Ahai; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 2; (2007); p. 493 - 502 View in Reaxys 2H

O

2H

2H 2

H

O

2H 2H

O 2H 2H

O 2H

NH 2 2H 2H

O 2H

Rx-ID: 11352116 View in Reaxys 26/38 Yield

Conditions & References Reaction Steps: 2 1: 86 percent / ammonium acetate; acetic acid / 3 h / Heating 2: lithium aluminum hydride / diethyl ether / 20 h / Heating With ammonium acetate, lithium aluminium tetrahydride, acetic acid in diethyl ether

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Xu, Ya-Zhu; Lin, Huei-Ru; Lua, Chang-Ahai; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 2; (2007); p. 493 - 502 View in Reaxys 2H

O

2H 2

H

O

2H

2H

2H 2H

O

2H

NH 2

2

H

2H 2H

O 2H

Rx-ID: 11374214 View in Reaxys 27/38 Yield

Conditions & References Reaction Steps: 3 1: 73 percent / titanium tetrachloride / CH2Cl2 / 0.25 h / 20 °C 2: 86 percent / ammonium acetate; acetic acid / 3 h / Heating 3: lithium aluminum hydride / diethyl ether / 20 h / Heating With ammonium acetate, lithium aluminium tetrahydride, titanium tetrachloride, acetic acid in diethyl ether, dichloromethane Xu, Ya-Zhu; Lin, Huei-Ru; Lua, Chang-Ahai; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 2; (2007); p. 493 - 502 View in Reaxys

O

O

H 2N

H 2N Cl

H

O

O

Rx-ID: 19066313 View in Reaxys 28/38 Yield

Conditions & References Reaction Steps: 3 1: 74 percent 2: 58 percent 3: 65 percent / 15percent NaOH / 14 h / Ambient temperature With sodium hydroxide Glennon, Richard A.; Seggel, Mark R.; Soine, William H.; Herrick-Davis, Katherine; Lyon, Robert A.; Titeler, Milt; Journal of Medicinal Chemistry; vol. 31; nb. 1; (1988); p. 5 - 7 View in Reaxys

O

O H 2N

O

Cl

NH F

F

O

H

O

F

Rx-ID: 19076246 View in Reaxys 29/38 Yield

Conditions & References Reaction Steps: 2 1: 58 percent 2: 65 percent / 15percent NaOH / 14 h / Ambient temperature With sodium hydroxide Glennon, Richard A.; Seggel, Mark R.; Soine, William H.; Herrick-Davis, Katherine; Lyon, Robert A.; Titeler, Milt; Journal of Medicinal Chemistry; vol. 31; nb. 1; (1988); p. 5 - 7 View in Reaxys

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O

O

H 2N

HO

O

O

Rx-ID: 16001262 View in Reaxys 30/38 Yield

Conditions & References Reaction Steps: 2 1: 97 percent / pyridine / 55 °C 2: 90 percent / liq. NH3 / 8 h / 50 - 60 °C With pyridine, ammonia, 1: Tosylation / 2: Substitution Yutilov; Malyutina; Shcherbina; Kirillova; Russian Journal of Applied Chemistry; vol. 72; nb. 10; (1999); p. 1787 1792 View in Reaxys Reaction Steps: 2 1: 97.2 percent / pyridine / 20 h / 0 - 5 °C 2: 70 percent / liq. NH3 With pyridine, ammonia, 1: Substitution / 2: Substitution Yutilov; Malyutina; Shcherbina; Kirillova; Russian Journal of Applied Chemistry; vol. 72; nb. 10; (1999); p. 1787 1792 View in Reaxys Reaction Steps: 2 1: 87 percent / pyridine 2: 65 percent / liq. NH3 With pyridine, ammonia, 1: Substitution / 2: Substitution Yutilov; Malyutina; Shcherbina; Kirillova; Russian Journal of Applied Chemistry; vol. 72; nb. 10; (1999); p. 1787 1792 View in Reaxys

H O

O O H

NH

O

H 2N

O

HN H

O

O

Rx-ID: 1378532 View in Reaxys 31/38 Yield

Conditions & References (i) H2, Pd-C, (ii) PhNCS, (iii) CF3CO2H, Multistep reaction Aldous,F.A.B. et al.; Journal of Medicinal Chemistry; vol. 17; (1974); p. 1100 - 1111 View in Reaxys

H O

O O H

NH

O

H 2N

O

HN H

O

O

Rx-ID: 1378533 View in Reaxys 32/38

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Yield

Conditions & References (i) H2, Pd-C, (ii) PhNCS, (iii) CF3CO2H, Multistep reaction Aldous,F.A.B. et al.; Journal of Medicinal Chemistry; vol. 17; (1974); p. 1100 - 1111 View in Reaxys

O

H

H 2N

O

H 2N O

O

Rx-ID: 22640506 View in Reaxys 33/38 Yield

Conditions & References Reaction Steps: 2 2: (i) H2, Pd-C, (ii) PhNCS, (iii) CF3CO2H Aldous,F.A.B. et al.; Journal of Medicinal Chemistry; vol. 17; (1974); p. 1100 - 1111 View in Reaxys

O

H

H 2N

O

H 2N O

O

Rx-ID: 22640507 View in Reaxys 34/38 Yield

Conditions & References Reaction Steps: 2 2: (i) H2, Pd-C, (ii) PhNCS, (iii) CF3CO2H Aldous,F.A.B. et al.; Journal of Medicinal Chemistry; vol. 17; (1974); p. 1100 - 1111 View in Reaxys O

O

O

O

H 2N

N O O

O

Rx-ID: 4229271 View in Reaxys 35/38 Yield

Conditions & References (i) NH4OAc, (ii) LiAlH4, THF, Multistep reaction Ho,B.T. et al.; Journal of Medicinal Chemistry; vol. 13; (1970); p. 26 - 30 View in Reaxys O H 2N

O

Rx-ID: 6591755 View in Reaxys 36/38 Yield

Conditions & References /BRN= 2094096/ Govindachari; Lakshmikantham; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 46; (1957); p.

406,408 View in Reaxys entspr.Nitrostyrol, H2

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Harmon et al.; Organic Preparations and Procedures International; vol. 2; nb. 1; (1970); p. 25; ; vol. 72; nb. 90607s; (1970) View in Reaxys

H

O

H 2N

O

Rx-ID: 8021393 View in Reaxys 37/38 Yield

Conditions & References entspr. α-Phenethylamin, H2 Patent; Univ. Iowa; US4000197; (1976); ; vol. 86; nb. 139599 View in Reaxys

H

O

H 2N

O

Rx-ID: 8021394 View in Reaxys 38/38 Yield

Conditions & References entspr. α-Phenethylamin, H2 Patent; Univ. Iowa; US4000197; (1976); ; vol. 86; nb. 139599 View in Reaxys

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