(E)-N-(4'-chlorobiphenyl-4-yl)-3-[4-(4-methylpiperidin-1-ylmethyl)phenyl]acrylamide → N-(4'-chlorobiphenyl-4-yl)-3-[4-(4-methylpiperidin-1-ylmethyl)phenyl]propionamide

HRID 735183Notes

Reaction equation

HRID 735183 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:32])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]4)=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>[Ni].C(OCC)(=O)C.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:32])[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:26][CH2:27][CH:28]([CH3:31])[CH2:29][CH2:30]4)=[CH:20][CH:19]=3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 57845736(E)-N-(4'-chlorobiphenyl-4-yl)-3-[4-(4-methylpiperidin-1-ylmethyl)phenyl]acrylamide

Product 1

HCID 57845688N-(4'-chlorobiphenyl-4-yl)-3-[4-(4-methylpiperidin-1-ylmethyl)phenyl]propionamide

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture of 80 mg (0.18 mmol) of (E)-N-(4′-chlorobiphenyl-4-yl)-3-[4-(4-methylpiperidin-1-ylmethyl)phenyl]acrylamide and 20 mg of Raney nickel in 15 mL of ethyl acetate and 15 mL of methanol is hydrogenated for 1 hour at 50 psi and ambient temperature. The catalyst is filtered off, the filtrate is evaporated to dryness and stirred with diisopropylether. Yield: 40 mg (49.7% of theory); melting point: 150° C.-151° C.; C28H31ClN2O (M=447.02); calc.: molecular ion peak (M+H)+: 447/449; found: molecular ion peak (M+H)+: 447/449; Rf value: 0.5 (silica gel, dichloromethane/methanol (10:1)).

Workup

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

Sources & evidence

ORD record
ord-8542919ad1bb4c79aa5b0530fbf1fa8f
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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