Hydrochloric Acid → 4-[4-Azatricyclo(4.3,1.13,8)undecan-4-yl]-2,2-diphenylbutanenitrile

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Reaction Steps

To a solution of 18 parts of α-phenylbenzeneacetonitrile in 140 parts of dry toluene is added, with stirring under nitrogen, approximately 4 parts of a 57% dispersion of sodium hydride in oil. The resultant mixture is heated to 90° and stirred thereat under nitrogen for 3/4 hr. The yellow-green flocculent suspension which eventuates is cooled to around 65°, whereupon 20 parts of 4-(2-chloroethyl)-4-azatricyclo[4.3.1.13,8 ]undecane [preparable by mixing the hydrochloride thereof (U.S. Pat. No. 3,845,038) with excess aqueous sodium carbonate, extracting the mixture with toluene, and consecutively washing the extract with water, drying it over anhydrous sodium sulfate, filtering out the drying agent, and removing the solvent by vacuum distillation] in 85 parts of dry toluene is introduced, with stirring, during 15 minutes. The mixture thus obtained is stirred for 2 hours at 90°-100°. The yellow-orange solution which results is cooled to room temperature, at which point 20 parts of water is stirred in. Aqueous and organic phases are separated, the aqueous phase is extracted with toluene and then discarded, and the extract and organic phases are combined and thereupon consecutively washed with water, dried over anhydrous sodium sulfate, and filtered. The filtrate is stripped of solvent by vacuum distillation, affording 4-[4-azatricyclo(4.3,1.13,8)undecan-4-yl]-2,2-diphenylbutanenitrile as the residue. The product has the formula ##STR9##

Provenance & Evidence