Acetic Acid → 3-(dimethylaminomethyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-cyanobenzaldehyde (2.50 g, 19 mmol) in MeOH:AcOH (25 ml, 99:1) was added dimethyl amine (2.5 ml, 50 mmol) at 0° C., followed by NaBH3CN (1.80 g, 29 mmol). The mixture was stirred at 0° C. for 18 hours, then evaporated, taken up in EtOAc, washed with 5% KHCO3, brine filtered (Whatman® 1 PS phase separator) and evaporated. The residue was purified by flash chromatography on silica gel (eluant EtOAc:MeOH 98:2 v/v) to give the title compound (1.15 g, 38 %).

Provenance & Evidence