Furfurylamine → 4-(Furan-2-yl)butan-1-amine

Participants

Reaction Steps

A solution of furfurylamine (1.0 g) in dry DMF (3 ml) was added to a cooled (0°-5° C.) stirred suspension of sodium hydride (60% dispersion; 0.46 g) in DMF (5 ml). After 15 minutes, a solution of 1-bromopropane (1.3 g) in dry DMF (2 ml) was added over 5 minutes. Stirring was continued for 1 h and the reaction mixture was then allowed to warm to room temperature and stirred overnight. The reaction was quenched by the addition of dilute hydrochloric acid. Aqueous sodium hydrogen carbonate solution (100 ml) was then added and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with water, brine and then dried (magnesium sulphate) and evaporated in vacuo. The residue was distilled under reduced pressure to furnish the title compound (0.21 g) as a colourless liquid.

Provenance & Evidence