4-Methylmorpholine → 8-bromo-N-butyl-N-methyl-octanamide

Participants

Reaction Steps

9.1 ml of N-methylmorpholine and then 10.4 ml of isobutyl chloroformate were added dropwise at -10° C. to -15° C. to a solution of 5 g of 8-bromo octanoic acid in 200 ml of methylene chloride. The mixture was stirred for 30 minutes at -10° C. to -15° C. and then at this temperature, 13 ml of N-methylbutylamine were added. The mixture was allowed to rise ambient temperature and stood for 40 minutes. Then, 150 ml of a saturated solution of sodium bicarbonate were added and the mixture was stirred for 10 minutes. After decanting, extraction was done with methylene chloride and the extracts were washed with a saturated solution of sodium chloride, dried and evaporated to dryness under reduced pressure. The residue was chromatographed on silica (eluant: methylene chloride-acetone 95-5) to obtain 6.14 g of the expected product.

Provenance & Evidence