N-((1-(cyanomethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide → N-((1-(2-aminoethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

HRID 1046549Notes

Reaction equation

HRID 1046549 reaction equation
[C:1]([CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=2)[CH2:6][CH2:5]1)#[N:2]>CO.[Ni]>[NH2:2][CH2:1][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:14]=2)[CH2:8][CH2:9]1

Participants

4

Reactant 1

HCID 86636686N-((1-(cyanomethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 57993201N-((1-(2-aminoethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Hydrogenation flask charged with a solution of N-((1-(cyanomethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide (2.80 g, 7.13 mmol) in methanol (20 mL) and Raney nickel (˜1 g, rinsed with methanol). The flask was shaken at room temperature under hydrogen (40 psi) overnight. The reaction mixture was then filtered through a celite cake, and the filtrate was concentrated to give sticky foam which was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered through a celite cake
  2. concentrationthe filtrate was concentrated
  3. customto give sticky foam which
  4. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-6c4bbf9e003542d98988669e759ef763
Source dataset
uspto-grants-2013_10
Patent number
US08569344B2

Reaction notes

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