Indriline is a central nervous system stimulant with antidepressant activity and application in the treatment of gastric ulcers.
A patent using this chemical is assigned to:[1] Pharmacology.[2]
Synthesis
The chemical synthesis of indriline has been described:[3][4]
Indriline synthesis
Treatment of 3-phenylindene [1961-97-3] (1) with n-butyl lithium and dimethylamino-2-choroethane gave indriline as well as some inactive isomer. Based on neighboring group participation (NGP), the reaction intermediate is presumably an aziridinium ion[4]
According to Molbase the number of routes for preparing the starting 3-phenylindene is rich. For example from dihydrochalcone.[5]
A more classical synthesis is also described in a Pyrophendane patent.
References
↑Dungan K, Lish P, "Process of treating peptic ulcer with a non-anticholinergic agent", US patent 3743746, issued 1970
↑"[On the central and peripheral pharmacological properties of 1-(2 dimethylaminoethyl)-1-phenylidene]" (in French). Therapie23 (5): 1135–46. 1968. PMID4387506.
↑"Phenylindenes and phenylindans with antireserpine activity". Journal of Medicinal Chemistry10 (3): 418–428. May 1967. doi:10.1021/jm00315a029. PMID22185145.
↑"Friedel-Crafts-type cyclodehydration of 1,3-diphenyl-1-propanones. Kinetic evidence for the involvement of dication.". Journal of the American Chemical Society116 (6): 2312-2317. March 1994. doi:10.1021/ja00085a010.
