Ammonia → 2-(3,4-dimethoxyphenyl)-2-methylpropan-1-amine

HRID 1368192Notes

Reaction equation

HRID 1368192 reaction equation
N.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]([CH3:16])([CH3:15])[C:13]#[N:14])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]>[Ni]>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]([CH3:16])([CH3:15])[CH2:13][NH2:14])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 102198982-(3,4-dimethoxyphenyl)-2-methylpropanenitrile

Product 1

HCID 122597152-(3,4-dimethoxyphenyl)-2-methylpropan-1-amineYield 89.1%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A conventional alkylation reaction was carried out using a dimethylformamide solution (10 ml) of 1.77 g of 2-(3,4-dimethoxyphenyl)acetonitrile, 1.00 g of sodium hydride and 4.26 g of methyl iodide to give 1.78 g of 2-(3,4-dimethoxyphenyl)-2-methylpropionitrile. A conventional catalytic hydrogenation reaction was carried out using an ethanolic solution (30 ml) of 1.75 g of 2-(3,4-dimethoxyphenyl)-2-methylpropionitrile, 3.0 ml of an aqueous 28% ammonia solution and 4.3 g of Raney nickel to give 1.59 g of 2-(3,4-dimethoxyphenyl)-2-methylpropylamine. Then, a conventional cyclization reaction was carried out using a formic acid solution (8 ml) of 1.58 g of 2-(3,4-dimethoxyphenyl)-2-methylpropylamine and 0.252 g of paraformaldehyde to give 1.34 g of 6,7-dimethoxy-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline as a pale yellow oily substance. A conventional alkylation reaction was carried out using a solution (10 ml) of 1.77 g of 2-(3,4-dimethoxyphenyl)acetonitrile in dimethylformamide, 1.00 g of sodium hydride and 4.26 g of methyl iodide to give 1.78 g of 2-(3,4-dimethoxyphenyl)-2-methylpropionitrile.

Workup

  1. customA conventional catalytic hydrogenation reaction

Sources & evidence

ORD record
ord-808bd8b89aef45fbb62c5e2f7cfc2718
Source dataset
uspto-grants-2003_06
Patent number
US06573279B1

Reaction notes

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