Benzylamine → HCID 18963780, compound

Participants

Reaction Steps

A solution of 5-methoxy-3-(1-methylethoxy)-2-benzofurancarboxylic acid (250 mg, 1.00 mmol) [Connor, et al., J. Med. Chem. 35, 935(1992)] and 1,1'-carbonyldiimidazole (211 mg, 1.30 mmol) in 7 mL of tetrahydrofuran is heated at reflux for 1 hour. The reaction solution is cooled to room temperature and benzylamine (0.66 mL, 6.00 mmol) is added and the reaction mixture is stirred at room temperature overnight. The reaction is diluted with ethyl acetate and washed with brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography eluting with ethyl acetate:hexane (1:3 to 1:1) provides 5-methoxy-3-(1-methylethoxy)-N-(phenylmethyl)-2-benzofurancarboxamide in 79% yield; mp=68°-69° C.

Provenance & Evidence