Phenylacetone → N-alpha-phenyl-ethyl-3,4-dimethoxy-amphetamine

HRID 2379020Notes

Reaction equation

HRID 2379020 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C@@H:12]([NH2:14])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CO[C:17]1[CH:18]=[C:19]([CH2:25][C@H:26](N)C)[CH:20]=[CH:21][C:22]=1OC.C1(CC(=O)C)C=CC=CC=1.[H][H]>[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH:14][CH:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:17][CH:18]=2)[CH3:26])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 7678PhenylacetoneHCID 11095534(2S)-1-(3,4-Dimethoxyphenyl)propan-2-amineHCID 117694083,4-Dma, (R)-HCID 178418361HCID 178418361, compound

Product 1

HCID 22918570N-alpha-phenyl-ethyl-3,4-dimethoxy-amphetamine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Weinges et al., Chem. Z., 94, 728 (1970), reported on a stereospecific synthesis of (S)-1-(3,4-dimethoxyphenyl)-2-aminopropane and (R)-1-(3,4-dimethoxyphenyl)-2-aminopropane in which initial reductive amination of the achiral 1-phenylpropan-2-one with either (R)- or (S)-α-phenethylamine in the presence of hydrogen and Raney nickel under high pressure produced 1-[1-(3,4-dimethoxyphenyl)prop-2-ylamino]1-phenylethane. Hydrogenolysis of this product then yielded (S)-1-(3,4-dimethoxyphenyl)-2-aminopropane or (R)-1-(3,4-dimethoxyphenyl)-2-aminopropane, respectively.

Sources & evidence

ORD record
ord-35f584c1fc0f427394d76ef467f39250
Source dataset
uspto-grants-1994_11
Patent number
US05360724

Reaction notes

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