Hydrochloric Acid → Anandamide

Temperature

-15 °C

Arachidonic acid (152 mg, 0.5 mmol) and triethylamine (52 mg, 0.51 mmol) were dissolved in 3 ml of dry acetonitrile and chilled to −15° C., and 70 mg (0.51 mmol) of butyl chloroformate was added. After 30 min, the mixture free of the precipitated triethylamine hydrochloride was pipetted in a solution of 2-aminoethanol (61 mg, 1 mmol) in 1 ml of methanol, stirring was continued for 15 min at −15° C., then the mixture obtained was allowed to warm to room temperature. After 2 h, 0.5 M HCl was added, and the mixture was extracted with ether (20 ml). The extract was washed with water, then dried with Na2SO4, and evaporated under reduced pressure. The residue was dissolved in 2 ml of chloroform and purified by column (2×2 cm) chromatography on aluminum oxide (basic, Brockmann II). Elution of the column with chloroform-methanol (9:1 v/v) and evaporation of the appropriate fractions gave 165 mg (95%) of desired N-arachidonoylaminoethan-2-ol as oil: TLC (system A) Rf 0.4.

1. waitwas continued for 15 min at −15° C.
2. customthe mixture obtained
3. temperatureto warm to room temperature
4. waitAfter 2 h
5. extractionthe mixture was extracted with ether (20 ml)
6. washThe extract was washed with water
7. dry with materialdried with Na2SO4
8. customevaporated under reduced pressure
9. dissolutionThe residue was dissolved in 2 ml of chloroform
10. custompurified by column (2×2 cm) chromatography on aluminum oxide (basic, Brockmann II)
11. washElution of the column
12. customwith chloroform-methanol (9:1 v/v) and evaporation of the appropriate fractions

ORD record

ord-ffd8f23f200a40e8bb9dd37434734a94

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06274747B1