N-(2-phenylethyl)acetamide → Ethyl beta-oxo-beta-[4-(2-acetamidoethyl)-phenyl]-propionate

Participants

Reaction Steps

N-Acetyl-phenethylamine is reacted with ethyl malonate chloride to give ethyl β-oxo-β-[4-(2-acetamidoethyl)-phenyl]-propionate (m.p. 89°-92° C.), which is reduced to ethyl β-[4-(2-acetamidoethyl)-phenyl]-propionate (m.p. 96°-98° C.) and this then subjected to alkaline saponification to give β-[4-(2-aminoethyl)-phenyl]-propionic acid (m.p. 270°-272° C.) followed by esterification to give the desired ethyl ester hydrochloride.

Provenance & Evidence