2-(2-Cyclopropylpyrimidin-5-yl)-2-(4,4-difluoropiperidin-1-yl)acetonitrile → 2-(2-Cyclopropylpyrimidin-5-yl)-2-(4,4-difluoropiperidin-1-yl)ethanamine

HRID 514887Notes

Reaction equation

HRID 514887 reaction equation
[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([CH:10]([N:13]3[CH2:18][CH2:17][C:16]([F:20])([F:19])[CH2:15][CH2:14]3)[C:11]#[N:12])=[CH:6][N:5]=2)[CH2:3][CH2:2]1>CO.[Ni]>[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([CH:10]([N:13]3[CH2:18][CH2:17][C:16]([F:19])([F:20])[CH2:15][CH2:14]3)[CH2:11][NH2:12])=[CH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 867160032-(2-Cyclopropylpyrimidin-5-yl)-2-(4,4-difluoropiperidin-1-yl)acetonitrile

Product 1

HCID 867160022-(2-Cyclopropylpyrimidin-5-yl)-2-(4,4-difluoropiperidin-1-yl)ethanamineYield 8.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(2-cyclopropylpyrimidin-5-yl)-2-(4,4-difluoropiperidin-1-yl)acetonitrile (3.50 g, 126 mmol), Raney Ni (3.50 g) and NH3H2O (10 mL) in MeOH (150 mL) was degassed and purged with argon and H2, then stirred at room temperature under H2 (50 Psi) for 4 hours. The reaction mixture was filtered and concentrated in vacuum to give 2-(2-cyclopropylpyrimidin-5-yl)-2-(4,4-difluoropiperidin-1-yl)ethanamine as a yellow oil (3.10 g), which was used directly for next step without further purification.

Workup

  1. customwas degassed
  2. custompurged with argon and H2
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-9dfa12fe697d4c3ab65a894b7aa829a6
Source dataset
uspto-grants-2015_08
Patent number
US09108938B2

Reaction notes

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