Phenethyl bromide → 1-Benzothiophene-2-carboxamide

Participants

Reaction Steps

N-(2-Aminoethyl)-3-methoxybenzo[b]thiophene-2-carboxamide (1.56 g) was dissolved in dimethyl fomamide (50 ml) and triethylamine (0.63 g) added. To this stirred solution was added phenethylbromide (1.27 g) and left overnight at ambient temperature. Ice-water was added, and the product extracted with ethyl acetate (3×50 ml). Organic fractions were collected, washed with water (4×50 ml),dried, filtered to yield, after removing the solvent, a clear oil. Flash chromatography eluting with 5% methanol-dichloromethane gave 3-methoxy-N-<2-[N- (2-phenylethyl)amino]ethyl>-benzo[b]thiophene-2-carboxamide which was converted to its hydrochloride.

Provenance & Evidence