Potassium Iodide → 2,2-Diphenyl-4-piperidin-1-ylbutanenitrile

Participants

Reaction Steps

To a warmed mixture of 1.96 parts piperidine, 1.91 parts potassium iodide and 25 parts deionized water under a nitrogen atmosphere is added 3.46 parts potassium bicarbonate and 7.51 parts of 2,2-diphenyl-4-bromobutyronitrile. The mixture is heated to reflux and maintained thereat for 4.5 hours. After cooling to room temperature, the reaction mixture is extracted three times with 14 part portions of ethyl ether. The ether extracts are combined, and extracted six times with 25 parts by volume portions of dilute acetic acid solution. The acid extracts are combined, basified to about pH 10 - 12 with 50% sodium hydroxide solution, and again extracted with ethyl ether. The ether extracts are combined and dried over anhydrous potassium carbonate. Removal of the solvent affords 2,2-diphenyl-4-piperidinobutyronitrile, identical to the product of Example 22, in a 75.3% yield.

Provenance & Evidence