Cyclopropylamine → 4-Bromo-2-cyclopropylaminomethyl-benzoic acid isopropyl ester

Participants

Reaction Steps

A stirred, cooled (ice bath) solution of 4-bromo-2-bromomethyl-benzoic acid isopropyl ester (Intermediate 118, 5.1 g, 15.17 mmol) in acetonitrile (25 mL) was treated with cyclopropyl amine (2 mL, 28.9 mmol). The reaction mixture was allowed to warm to ambient temperature. After 2 h, the volatiles were evaporated in vacuo, the residue was diluted with water and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230–400 mesh) using 4–20% ethyl acetate in hexane as the eluent to afforded the title product (1.33 g, 28%).

Provenance & Evidence