Structure-activity relationships in psychotomimetic phenylalkylamines.

tected with a drying tube. A solution of phosgene (55 ml, 12.5% in benzene) was then added with vigorous stirring. The reaction was cooled for an additional 10 min and was then kept at room temperature for 1 hr. The reaction mixture was cooled again, treated with 100-ml portions of 1 N HCl until free of amine, and then rinsed successively with 8% NaHCOs and water, dried, and evaporated, giving a thick oil which solidified in methanol. Recrystallization from 95% ethanol to give a crystalline product, 1.08 g (46.5%), mp 110-113”. Anal. (CZIHISF~NOZ-HZO) C, H, N. Acknowledgments. We wish to thank Drs. E. A. Steck and T. R. Sweeney for their counsel and for making available to us a generous supply of a number of key starting materials. The skillful technical assistance of Ms. E. Hayes, G. Millar, and Mr. W. Smolnycki in the preparation of several intermediates is gratefully acknowledged. The authors also wish to thank Dr. C. B. Boyce for valuable suggestions and discussions of the photochemical approaches.