Vol. 68 tion was extracted twice more with 50-cc. portions of ether. The combined ether extracts were dried over magnesium sulfate and the ether was removed on the steam cone.Excess diamine was distilled under reduced pressure; 8.3 g. was collected at 81-82°( 14 mm.) and 5.5 g. at 45-48°( 0.5 mm.). The residue began to crystallize even before all the diamine had distilled so it was purified by recrystallization rather than by distillation. After treating with 3 g. of decolorizing charcoal in 200 cc. of boiling benzene, the benzene solution was concentrated to about 40 cc. and 300 cc. of low-boiling petroleum ether was added with stirring. The mixture was cooled and the light tan crystalline product was collected in a filter; 24.5 g. (82%), m. p. 113-119°. This product was recrystallized twice from Skellysolve B (b. p. 60-68°), yielding 20.0 g of white plates, m. p. 122-123°.
Vol. 68 chloride to make the solution acidic to congo red paper. The yields were determined largely by the recovery which each recrystallization solvent permitted, as the condensation reaction itself was almost quantitative.One derivative was prepared by using 2-hydroxy-3diethylaminopropylamine as the side-chain.Whenever the dihydrochloride was obtained as a hydrate, a sample of the anhydrous form (very hygroscopic) was prepared for characterization by heating the hydrate at 140°, or by recrystallizing it from an inert solvent containing thionyl chloride.12-(3 '-Diethylaminopropylamino) -benz [a ¡acridin e Dihydrochloride.-This compound was prepared in a manner analogous to the procedure used for the corresponding benz-[c]acridine derivatives. The yield after two recrystallizations from propanol-dibutyl ether was 31% of very small, yellow needles, m. p. 250-252°b y the instantaneous method.
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.