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

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Reaction Conditions

Reaction Steps

To a stirred mixture of 78.5 parts of 2,2-diphenyl-4-bromobutyronitrile, 19.7 parts of potassium iodide and 30.0 parts of 1,4-diazabicyclo[4.3.0]nonane is added 70 parts of water and 19.3 parts of potassium hydroxide under a nitrogen atmosphere. The mixture is stirred and heated to 75° - 80° C. and then further heated to reflux (108° - 112° C.). After 3.5 hours of heating at reflux, the mixture is cooled to about 25° C. and 180 parts of ethyl ether added. The resulting organic layer is extracted once with a 20% solution of hydrochloric acid in water followed by a further extraction with 6% solution of hydrochloric acid in water. The aqueous extracts are then combined and basified to pH 11.0 with a 50% solution of sodium hydroxide in water. The resulting oil is extracted with three 110 parts portions of ethyl ether. The ether extracts are combined, 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, is obtained in 89% yield. Correction of this yield to reflect the purity of the 1,4-diazabicyclo[4.3.0]nonane (96%) results in a yield of 93% for this reaction. This product boils at about 190° - 210° C. at 0.1 mm. pressure and is represented by the following structural formula. ##STR9##

Provenance & Evidence