Octylamine → N-octylpropiolamide

Participants

Reaction Steps

To a stirred, cooled (-30° C.) solution of 18.42 g (0.143 mol) of n-octylamine in 25 ml of aqueous methanol was added 10 g (0.119 mol) of methyl propiolate dropwise. After the addition the reaction mixture was allowed to warm to room temperature and stir for 12 h. The reaction mixture was poured into ice-cold 10% aqueous hydrochloric acid and extracted with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate, brine, and dried over magnesium sulfate. Filtration and removal of solvents gave a crude mixture which was purified by column chromatography (Merck 60® silica gel, 25% ethyl acetate/hexane eluant) to give N-octylpropiolamide.

Provenance & Evidence