Synthesis and Antimuscarinic Activity of 2-(N-(Ethyl)-(N-Beta- Hydroxyethyl)) Aminoethyl 2,2-Diphenylpropionate, a Metabolite of Aprophen
Abstract
The preparation of 2-(N-(ethyl)-(N-beta-hydroxyethyl)aminoethyl 2,2- diphenylpropionate (1), a metabolite of aprophen 12-diethylaminoethyl 2,2- diphenylpropionate) is described. Hydrolysis of 2-(2-chloroethyl) ethylaminolethyl 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 approx. 10-fold less potent than the parent compound aprophen.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jun 01, 1993
- Accession Number
- ADA269081
Entities
People
- Haim Leader
- Lawrence R. Phillips
- Nesbitt D. Brown
- Richard K. Gordon
- Ruthann M. Smejkal
Organizations
- Walter Reed Army Institute of Research