(E)-3-(4'-chlorobiphenyl-4-yl)-N-(4-piperidin-1-ylmethylphenyl)acrylamide → 3-(4'-Chloro-biphenyl-4-yl)-n-(4-piperidin-1-ylmethyl-phenyl)-propionamide

HRID 898619Notes

Reaction equation

HRID 898619 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:21][CH:20]=3)=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>[Ni].CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:21][CH:20]=3)=[O:17])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 9980157(E)-3-(4'-chlorobiphenyl-4-yl)-N-(4-piperidin-1-ylmethylphenyl)acrylamide

Product 1

HCID 596915573-(4'-Chloro-biphenyl-4-yl)-n-(4-piperidin-1-ylmethyl-phenyl)-propionamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 0.200 g (0.464 mmol) (E)-3-(4′-chloro-biphenyl-4-yl)-N-(4-piperidin-1-ylmethyl-phenyl)-acrylamide (Example 172) and 100 mg Raney nickel in 50 mL EtOAc was hydrogenated at RT and 50 psi. The catalyst was filtered off, the filtrate was evaporated down i. vac. and the residue was triturated with ether. The precipitate was filtered off, washed with ether and dried at 50° C. i. vac.

Workup

  1. customwas hydrogenated at RT
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated down i
  4. customand the residue was triturated with ether
  5. filtrationThe precipitate was filtered off
  6. washwashed with ether
  7. customdried at 50° C. i

Sources & evidence

ORD record
ord-41e9c4842206472690400c5b667e3bb9
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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