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 methylene chloride (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 addition 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) as the eluent to give the purified title compound as a white solid (9.77 g, 83%).

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-336a2508512f4012bfb7216b54d52b88

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998419