Propionic Acid → N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

Participants

Reaction Steps

To a stirred black solution of (rac)-4-bromo-5,6,7,8-tetrahydroisoquinolin-8-amine (317 mg, 1.4 mmol) and propionic acid (115 μL, 1.54 mmol) in CH2Cl2 (7.0 mL) at 0° C. was added EDCI (295 mg, 1.54 mmol), stirring was continued over night and the reaction mixture was allowed to warm up to RT. The reaction mixture was poured on aq. 10% KH2PO4 solution followed by extraction with AcOEt (3×). The organic phases were washed once with aq. 10% KH2PO4, aq. sat. NaHCO3 and with aq. sat. NaCl solution. The combined organic phases were dried over Na2SO4, filtered, evaporated and purified by precipitation CH2Cl2/n-pentane to afford the title compound (365 mg, 92%) as light brown solid. MS: 283.0 (M+H+, 1 Br).

Provenance & Evidence