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Process description for the preparation of Ericamide ((E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide)

IP.com Disclosure Number: IPCOM000240459D
Publication Date: 2015-Jan-30
Document File: 2 page(s) / 85K

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The IP.com Prior Art Database

Abstract

Executive Summary: This publication describes the process to prepare (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl) acrylamide named “Ericamide” from 3,4-dimethoxy cinnamic acid and 4-methoxy phenethylamine in the presence of high boiling solvent like Limonene

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Process description for the preparation of Ericamide ((E)-3-(3,4-

dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide)

Executive Summary: This publication describes the process to prepare (E)-3-(3,4-

dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide named "Ericamide" from 3,4-dimethoxy

cinnamic acid and 4-methoxy phenethylamine in the presence of high boiling solvent like

Limonene


(E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide is synthesized by heating 3,4- dimethoxy cinnamic acid and 4-methoxy phenethylamine at high temperature in the presence of a solvent having a boiling point of at least 150°C (such as Limonene which has the advantage of being also a flavor compatible solvent) (e.g. see scheme 1). The formed water is allowed to distill out of the reaction mixture. At the end of the reaction, the formed amide is crystallized from reaction mixture (after cooling and addition of an alcohol) then filtered, washed and dried. Very pure (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide (trans isomer) is thus obtained.

Scheme 1

The reaction is best run with a large amount of solvent, typically with 500% by weight compared to the dimethoxy cinnamic acid. As mentioned above, other solvents may be employed, such as other flavor compatible terpenes and also hydrocarbon solvents such as decane, nonane or mesytilene. Reaction may also be realised with cyclohexane, heptane or toluene under pressure. Running the reaction at a lower temperature (164°...