After boiling off the acetone, 500 ml of ice water was added and the solution was saturated with NaCl. The reaction mixture was extracted (EUO) and the extract was dried (Na2C03).Stripping off the ether left a brown viscous residue. Trituration of the residue with MeOH yielded 4.2 g (31%) of IV, mp 121.5-122.5°(MeOH).The N-phenylpiperazines listed in Table I were synthesized by analogous procedures.l-(2-Bromo-4,5-dimethoxyphenyl)-4-(2-methyl-4,5-dimethoxypheny 1 )piperazine.-A solution of 31 g (0.05 mole) of II ditosylate and 25 g (0.15 mole) 4-methyl-5-aminoveratrole in 1 1. of 50% Me2C0~H20 -was refluxed for 2 days. A solid which precipitated during the course of the reaction was filtered. After washing (Et20) and recrystallization (¿-PrOH), it gave 4.2 g of white glistening flakes.l-(2-Bromo-4,5-dimethoxyphenyl)-4-tetramethyIenepiperazinium Chloride.-A solution of III (14 g) and 20 ml of pyrrolidine in 150 ml of THE was refluxed for 2 days. Filtration of the cooled reaction mixture gave 16 g of a tan solid. Extraction with hot z-PrOH left the piperazinium salt as a white solid (8.9 g).The piperazinium salts listed in Table II were prepared in a like manner.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.