Toluene → HCID 68120624, compound

Participants

Reaction Steps

To a solution of 41.3 g. (0.13 mole) of α,α-diphenyl-α-(1-isobutyl-3-pyrrolidinyl)acetonitrile in 120 ml. of dry toluene was added 11.2 g. (0.286 mole) of sodium amide in a 500 ml. round bottom flask equipped with a reflux condenser and mechanical stirrer. The stirred mixture was refluxed for 46 hours. A large excess of water was added slowly and the water layer separated and discarded after being extracted with ether which was combined with the organic layer. The organic layer was washed with water and extracted with an excess of 2 N hydrochloric acid. The acid extract was basified with sodium hydroxide and the oil which separated was extracted with ether. The ethereal solutions were combined, concentrated and the residue was distilled. Yield, 25.8 g. (68%); b.p. 150°-152° C/0.05 mm. To 11.2 g. (0.0382 mole) of the above product was added 4.45 g. (0.0382 mole) of maleic acid in 150 ml. of absolute alcohol. After the amine dissolved, 100 ml. of dry ether was added. On standing in the refrigerator for several days the solution yielded a white solid which was recrystallized from ethyl acetate. Yield, 10.5 g. (67.25%); m.p. 119°-120° C.

Provenance & Evidence