Cycloheptylamine → 2-Bromo-N-(cycloheptyl)acetamide

To a −20° C. solution of cycloheptylamine (6.37 mL, 50.0 mmol) and diisopropylethylamine (9.58 mL, 55.0 mmol) in CH2Cl2 (250 mL) was slowly added bromoacetyl bromide (4.78 mL, 55.0 mmol). The reaction mixture was warmed to room temperature over 20 minutes and stirred for an additional 30 minutes. The reaction mixture was diluted with water (100 mL) and stirred for an additional 30 minutes. The organic layer was separated, washed with water (3×100 mL), dried over magnesium sulfate and concentrated in vacuo to afford a beige solid (10.5 g). The crude material was further purified by silica gel flash column chromatography using hexane:ethyl acetate (1/1, v/v) as the eluent to give the purified title compound as an oil (9.77 g, 83%). 1H-NMR (Me2SO-d6): δ 8.20 (br d, 1H), 3.77 (s, 2H), 3.67 (m, 1H) and 1.8-1.3 (m, 12H). 13C-NMR (CDCl3): δ 164.01, 51.04, 34.59, 29.40, 27.80 and 23.87. Mass spectrum (FAB+) m/z 234/236 [M+H]+ and 256/258 [M+Na)+.

1. customTo a −20° C.
2. stirringstirred for an additional 30 minutes
3. customThe organic layer was separated
4. washwashed with water (3×100 mL)
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-f9b5692fd7d44b03ad97eae1c382d165

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06991902B2