SYNTHESIS OF COMPOUNDS WITH POTENTIAL PSYCHOTOMIMETIC ACTIVITY .4.

As a continuing study of structure-activity relationships of psychotomimetic agents, the N-methyl-3-piperidyl esters of evcloheptylphenylglycolic acid, ethynylphenylglycolic acid, and of acids derived from 1,2,3,3a,8,8ahexahydrocyclopent [a] indene were prepared. A new and improved method of esterification of disubstituted glycolic acids, involving treatment of their sodium salts with N-methyl-3-piperidyl tosylate, has been utilized. The methyl ester of 9-hydroxy-9a-methyl-1,2,3,4,4a,9a-hexahydrofluorene-9-carboxylic acid has been prepared, but extremely low yields did not permit further work with this compound. Biological test data are reported. © 1968, American Chemical Society. All rights reserved.