Palmitoylethanolamide → N-[2-(ethoxycarbonyl)oxyethyl]hexadecanamide

3.0 g of N-(2-hydroxyethyl) hexadecanamide (10 mmoles) was dissolved in 75 ml of tetrahydrofuran (THF) at 45° C. with stirring. 1.11 g of N-methylmorpholine (11 moles) and 1.19 g of ethyl chloroformate (11 moles) were added and the resulting mixture was stirred for a further 3 hours at ambient temperature. The mixture was then evaporated to dryness under vacuum. The residue was taken up with 50 ml of water and extracted 3 times with 30 ml of ethyl acetate; the organic phases were washed twice with 20 ml of water, recombined and evaporated to dryness. The residue was crystallized from 30 ml of tert-butylmethyl ether. The crystallizate was separated by filtration, washed twice with 5 ml of cold tert-butylmethyl ether and finally dried under a high degree of vacuum. The yield of the reaction was 93%.

1. stirringthe resulting mixture was stirred for a further 3 hours at ambient temperature
2. customThe mixture was then evaporated to dryness under vacuum
3. extractionextracted 3 times with 30 ml of ethyl acetate
4. washthe organic phases were washed twice with 20 ml of water
5. customevaporated to dryness
6. customThe residue was crystallized from 30 ml of tert-butylmethyl ether
7. customThe crystallizate was separated by filtration
8. washwashed twice with 5 ml of cold tert-butylmethyl ether
9. customfinally dried under a high degree of vacuum

ORD record

ord-88cf6f6a6afa4b9483b5499fbaa1b58c

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06864285B1