Allylamine → HCID 69218361, compound

Participants

Reaction Steps

A solution of benzoin (6.81 g, 32.1 mmol), allylamine (2 g, 35 mmol) and p-toulenesulfonic acid monohydrate (20 mg, cat.) in toluene (100 mL) was heated to 80° C. for 5 minutes. Malononitrile (2.12 g, 32.1 mmol) was then added and the reaction mixture was heated to reflux for 3 hours using a reflux condenser fitted with a Dean-Stark trap. The solution was then cooled, diluted with ethyl acetate (100 mL), extracted with sodium bicarbonate (conc., aq., 50 mL), hydrochloric acid (0.5 N, aq., 50 mL) and water (50 mL), dried, filtered and the filtrate was concentrated under reduced pressure. Chromatography (SiO2, ethyl acetate:hexane 1:2) afforded the title compound as a pale brown solid.

Provenance & Evidence