The preparation of 2-[N-(ethyl)-(N-beta-hydroxyethyl)]amino-ethyl 2,2-diphenylpropionate (1), a metabolite of aprophen [2-diethylaminoethyl 2,2-diphenylpropionate], is described. Hydrolysis of [2-(2-chloroethyl)ethylamino]ethyl acetate hydrochloride (2) in a basic solution, followed by acidic pH adjustment, gave the ethylcholineaziridinium ion (3) that upon treatment with 2,2-diphenylpropionic acid produced 1 in a 56% yield. Synthetic 1 was found to possess antimuscarinic activities, but was approximately 10-fold less potent than the parent compound aprophen.
Brown ND, Leader H, Phillips LR, Smejkal RM, Gordon RK, Chiang PK (1993) Synthesis and antimuscarinic activity of 2-[N-(ethyl)-(N-beta- hydroxyethyl)]aminoethyl 2,2-diphenylpropionate, a metabolite of aprophen J Pharm Sci82: 563-4
Brown ND, Leader H, Phillips LR, Smejkal RM, Gordon RK, Chiang PK (1993) J Pharm Sci82: 563-4