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

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.

1. customto rise ambient temperature
2. waitstood for 40 minutes
3. stirringthe mixture was stirred for 10 minutes
4. customAfter decanting
5. extractionextraction
6. washthe extracts were washed with a saturated solution of sodium chloride
7. customdried
8. customevaporated to dryness under reduced pressure
9. customThe residue was chromatographed on silica (eluant: methylene chloride-acetone 95-5)

ORD record

ord-d9341996e6f344c6aceb4b713a2261f1

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06790971B1