3,4-Dimethoxyaniline → N-(3,4-Dimethoxyphenyl)-8-[2-(3,4-dimethoxyphenyl)ethyl]-8-aza-bicyclo[3.2.1]octan-3-amine

Participants

Reaction Steps

To a stirred solution of 4 g (26 mmol) 3,4-dimethoxyaniline and 5 ml 14N methanolic HCl in 200 ml methanol, were added 5.7 g (20 mmol) of 8-[2-(3,4-dimethoxyphenyl)ethyl]-8-azabicyclo[3.2.1]octane-3-one (D1), followed by addition of 1 g (16 mmol) sodium cyanoborohydride. The reaction mixture was stirred overnight, slightly acidified and concentrated to dryness. The crude residue was filtered over a short column of silica gel using 95:5 methylene chloride:methanol. The expected fraction was triturated with ethyl acetate affording 4 g (47%) of the desired compound. mp.: 220° C. 1H NMR shows a mixture of two conformations of the title compound.

Provenance & Evidence