4-[3-(Dimethylamino)propoxy]benzonitrile → 3-[4-(Aminomethyl)phenoxy]-N,N-dimethylpropan-1-amine

HRID 1035955Notes

Reaction equation

HRID 1035955 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1>CO.[Ni]>[NH2:12][CH2:11][C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:15])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 118583624-[3-(Dimethylamino)propoxy]benzonitrile

Product 1

HCID 214653843-[4-(Aminomethyl)phenoxy]-N,N-dimethylpropan-1-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4-(3-(Dimethylamino)propoxy)benzonitrile (300 mg) in methanol (20 mL) was treated with Raney nickel (wet, 1.5 g) under H2 (30 psi) for 4 hour. The insoluble material was filtered off and the filtrate was concentrated to provide the title compound.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b8d6d6004db044edbc0ea654bcd59dd4
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

Loading…