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

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To a solution of (rac)-4-bromo-5,6,7,8-tetrahydro-isoquinolin-8-ylamine (intermediate A-2 [D]) (3.7 g, 16.3 mmol) and Et3N (3.3 g, 32.6 mmol) in DCM (50 mL) was added propionyl chloride (2.25 g, 24.4 mmol) at 0° C. The resulting reaction mixture was stirred for 3 hr before it was warmed up to room temperature and poured into water (50 mL) and extracted with DCM (2×50 mL). The combined organic layers were then dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography and afforded the title compound (4.29 g, 93% yield) as a white solid. MS: 283.0 (M+H+).

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