Azane;hydrate → 2-(Pyridin-4-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)ethanamine

HRID 512177Notes

Reaction equation

HRID 512177 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([C:10]2[CH:11]=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=2)[C:8]#[N:9])=[CH:3][CH:2]=1.N.O>CO.[Ni]>[N:1]1[CH:2]=[CH:3][C:4]([CH:7]([C:10]2[CH:11]=[N:12][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:14][CH:15]=2)[CH2:8][NH2:9])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 12896473Azane;hydrateHCID 867162032-(Pyridin-4-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrile

Product 1

HCID 867162042-(Pyridin-4-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)ethanamineYield 82.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(pyridin-4-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrile (360 mg, 1.36 mmol) and NH3.H2O (2 mL) in MeOH (30 mL) was hydrogenated with Raney Ni (700 mg) under H2 (50 Psi) for 5 h. The reaction mixture was filtered and concentrated to give 2-(pyridin-4-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)ethanamine (300 mg), which was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8afa8800b84a4ec183973c836b918eae
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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