Scalable synthesis of oleoyl ethanolamide by chemical amidation in a mixed solvent

Abstract Oleoyl ethanolamide is a lipid mediator that exhibits biological activity in animal and cell models. In this study, an effective process is described to synthesize oleoyl ethanolamide by chemical amidation with native oil used as an acyl donor in the presence of sodium methoxide. Reaction conditions were optimized. When the amidation reaction was conducted in a mixed solvent, by reacting 2 mmol high oleic sunflower oil and 20 mmol ethanolamine in the presence of 1.5 % sodium methoxide with agitation, >90 % fatty acid ethanolamide was formed after 3 h of reaction time. The fatty acid ethanolamide product was purified by a two‐step crystallization process to prepare oleoyl ethanolamide. Highly pure oleoyl ethanolamide was obtained in a 70.3 % molar yield. The novelty of the work is the use of native oil as acyl donor and the mixed solvent used as the reaction media. The use of native oil avoids the formation of ion pairs with ethanolamine that can occur in other synthesis routes.

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