(E)-N-(4'-methoxybiphenyl-4-yl)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylamide → N-(4'-methoxybiphenyl-4-yl)-3-(4-pyrrolidin-1-ylmethylphenyl)propionamide

HRID 735182Notes

Reaction equation

HRID 735182 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:31])/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>[Ni].CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:31])[CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:21][CH:20]=3)=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 57845721(E)-N-(4'-methoxybiphenyl-4-yl)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylamide

Product 1

HCID 57845839N-(4'-methoxybiphenyl-4-yl)-3-(4-pyrrolidin-1-ylmethylphenyl)propionamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A reaction mixture of 60 mg (0.14 mmol) of (E)-N-(4′-methoxybiphenyl-4-yl)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylamide and 10 mg of Raney nickel in 30 mL of methanol is hydrogenated for 4 hours. The catalyst is filtered off and the filtrate is evaporated to dryness. Yield: 56 mg (93.2% of theory); melting point: 185° C.-188° C.; C27H30N2O2 (M=414.55); calc.: molecular ion peak (M+H)+: 415; found: molecular ion peak (M+H)+: 415; Rf value: 0.29 (silica gel, dichloromethane/methanol/ammonia (90:10:1)).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-948bd2d2d97a4207af6da30e6560f25d
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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