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ChemicalBook CAS DataBase List ANANDAMIDE
94421-68-8

ANANDAMIDE synthesis

6synthesis methods

Arachidonic acid-rich microbial algal oil (43.69% arachidonic acid, and other fatty acids such as 6.68% palmitic acid, 5.81% stearic acid, 5.95% oleic acid, 8.93% linoleic acid, 2.27% linolenic acid, 4.2% arachidonic acid, 3.2% behenic acid, and 10.62%

-

Yield:94421-68-8 96%

Reaction Conditions:

Stage #1:all cis 5,8,11,14-eicosatetraenoic acid with 1,1'-carbonyldiimidazole in dichloromethane at 20; for 0.5 h;
Stage #2:ethanolamine in dichloromethane for 12 h;

Steps:

(21) General Procedure for Amide Coupling
General procedure: To a stirred solution of the fatty acid (1.0 mmol, 1.0 equiv.) inCH2Cl2 (5 mL) was added CDI (0.178 g, 1.1 mmol, 1.1 equiv.).After 30 min at room temperature, the amine (1.1 mmol, 1.1equiv.) was added. After 12 h, CH2Cl2 (25 mL) was added, followedby saturated aqueous NH4Cl. The mixture was acidified topH 2 by addition of HCl, the organic phase was separated, andthe aqueous layer was further extracted with CH2Cl2 (3 × 10mL). The organic phases were combined, dried over Na2SO4, filtered,and concentrated in vacuo, to give the amide.

References:

Johansson, Silje J. R.;Johannessen, Tonje;Ellefsen, Christiane F.;Ristun, Mali S.;Antonsen, Simen;Hansen, Trond V.;Stenstrom, Yngve;Nolsoe, Jens M. J. [Synlett,2019,vol. 30,# 2,art. no. ST-2018-D0672-L,p. 213 - 217] Location in patent:supporting information

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