1-Phenethylamine → 2,2-dimethoxy-N-(1-phenylethyl)ethanamine

Participants

Reaction Steps

A solution of α-methylbenzylamine (8.37 g, 0.069 mol) and bromoacetaldehyde dimethylacetal (11.67 g, 0.069 mol) in acetonitrile (150 ml) containing potassium carbonate (12.39 g, 0.09 mol) was heated at reflux for 2 days then cooled. The resulting precipitate was filtered off and the filtrate was concentrated in vacuo to give the crude product as an oil. Chromatography on silica gel eluting with ethyl acetate afforded the title compound as an oil (10.1 g). 1H NMR (400 MHz, CDCl3) δ(ppm): 7.31 (m, 3H), 7.23 (m, 2H), 4.43 (t, 1H), 3.75 (q, 1H), 3.35 (s, 3H), 3.31 (s, 3H), 2.63 (dd, 1H), 2.55 (dd, 1H), 1.36 (d, 3H).

Provenance & Evidence