Dimethylamine → N,N-Dimethylheptanamide

Ethylchloroformate (18.3 ml) was added slowly to a solution of heptanoic acid (20.0 g) and triethylamine (26.7 ml) in tetrahydrofuran (250 ml), maintained at -10°. The resulting mixture was stirred at 10° for 0.75 hour, cooled to 5° and a 33% solution of dimethylamine in ethanol (41.6 ml) added dropwise. This mixture was then allowed to warm to room temperature and stirred for 4 hours. The mixture was filtered and the filtrate evaporated to dryness. The residue was dissolved in chloroform (250 ml) and washed with 1% aqueous sodium carbonate solution (200 ml) and water, then dried and evaporated. The residual oil was chromatographed on silica gel to give N,N-dimethylheptanamide (14.1 g) as a colourless oil.

1. temperaturemaintained at -10°
2. temperaturecooled to 5°
3. stirringstirred for 4 hours
4. filtrationThe mixture was filtered
5. customthe filtrate evaporated to dryness
6. dissolutionThe residue was dissolved in chloroform (250 ml)
7. washwashed with 1% aqueous sodium carbonate solution (200 ml) and water
8. customdried
9. customevaporated
10. customThe residual oil was chromatographed on silica gel

ORD record

ord-71e2aa79daed492389ddb4bbb1e4438c

Source dataset

uspto-grants-1990_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04954339