Water → 2,2-Diphenyl-4-(1,4-diazabicyclo[4.3.0]non-4-yl)butyronitrile

Participants

Reaction Conditions

Reaction Steps

To 70.6 parts of 2,2-diphenyl-4-bromobutyronitrile is added 27 parts of 1,4-diazabicyclo[4.3.0]nonane, 63 parts of demineralized water and 15.5 parts of potassium hydroxide. The mixture is stirred and heated to 75° - 80° C. and then further heated to reflux. After 3.5 hours at reflux, the mixture is cooled to about 30° C. and 180 parts of ethyl ether is added. The aqueous layer is separated and discarded. The remaining ether layer is extracted three times with 100 parts by volume portions of 1% acetic acid in water, twice with 30% solutions of hydrochloric acid in water, and twice with 50% solutions of hydrochloric acid in water. The hydrochloric acid solution extracts are combined and basified to pH 11.0 with a 50% solution of potassium hydroxide in water. The resulting oil is extracted with three 150 part portions of chloroform. The chloroform extracts are combined, washed with 100 parts of a saturated sodium chloride solution, dried over anhydrous potassium carbonate, and stripped of solvent under reduced pressure. The resulting product, 2,2-diphenyl-4-(1,4-diazabicyclo[4.3.0]non-4-yl)butyronitrile, identical to the product of Example 7, is obtained in 86% yield. Correction of this yield to reflect the purity of the 1,4-diazabicyclo[4.3.0]-nonane (86.4%) results in a yield of 99.5% for this reaction.

Provenance & Evidence