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

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+).

1. customThe resulting reaction mixture
2. extractionextracted with DCM (2×50 mL)
3. customThe combined organic layers were then dried over anhy
4. filtrationNa2SO4, filtered
5. concentrationconcentrated in vacuo
6. customThe residue was purified by silica gel column chromatography

ORD-Eintrag

ord-7bab575ed6c643dd9eeeca2ac76da0ae

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09353081B2