Hydrochloric Acid → HCID 68146490, compound

Participants

Reaction Steps

20 G. of 4-(cis-2,2-dimethyl-5-phenyl-3-pyrrolidinyl)-pyridine (racemate) are dissolved under cool temperatures (5°-10° C.) in concentrated nitric acid and 50 ml. of cool concentrated sulfuric acid are slowly added. Thereafter, the reaction mixture is stirred for about 1 hour at 10°-15° C. and then poured on ice. The pH of the reaction mixture is then adjusted to pH 8-9 with 3N sodium hydroxide, also in the cold, and exhaustively extracted with methylenechloride. The combined extracts are dried over sodium sulfate and evaporated in a water pump vacuum to dryness. The product thereby obtained is a mixture of pyrrolidine with para and meta nitrophenyl substituents. The mixture is dissolved in 400 ml. warm ethanol. After the addition of 25 ml. concentrated hydrochloric acid and some ether, a mixture of dihydrochlorides (m-nitrophenyl and p-nitrophenyl, 8 to 2) is obtained. Fractional crystallization from ethanol yields 4-[cis-2,2-dimethyl-5-(m-nitrophenyl)-3-pyrrolidinyl]-pyridine dihydrochloride (racemate) with a melting point of 229°-232° C. (decomp.).

Provenance & Evidence