4-[(Dimethylamino)methyl]phenylacetonitrile → 2-{4-[(Dimethylamino)methyl]phenyl}ethan-1-amine

HRID 1820869Notes

Reaction equation

HRID 1820869 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[N:13])=[CH:7][CH:6]=1)[CH3:3]>N.[H][H].[Ni]>[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH2:13])=[CH:7][CH:6]=1)[CH3:3]

Participants

5

Reactant 1

HCID 157028704-[(Dimethylamino)methyl]phenylacetonitrile

Product 1

HCID 164950282-{4-[(Dimethylamino)methyl]phenyl}ethan-1-amine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 178418361HCID 178418361, compoundCatalystHCID 222AmmoniaSolvent

Procedure

3.60 g (20.7 mmol) of (4-dimethylaminomethylphenyl)acetonitrile (IX.1.a) is dissolved in 50 mL of methanolic ammonia and hydrogenated for 5 hours at 50° C. at a pressure of 3 bar with hydrogen and 0.45 g of Raney nickel as catalyst. Then the catalyst is filtered off and the solvent is eliminated. Yield: 3.60 g (98% of theory); Rf value: 0.20 (silica gel, methylene chloride/methanol=9:1); C11H18N2; EII mass spectrum: m/z=179 [M+H]+.

Workup

  1. filtrationThen the catalyst is filtered off

Sources & evidence

ORD record
ord-fba2b85c23f84da994f2d821eba8f279
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

Loading…