2,2-Diphenyl-4-piperidin-1-ylbutanenitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The mixture is heated to reflux maintained the reaction mixture is extracted three times with 14 part portions of ethyl ether extracted six times with 25 parts by volume portions of dilute acetic acid solution again extracted with ethyl ether dried over anhydrous potassium carbonate Removal of the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.96 Parts piperidine, 1.91 parts potassium iodide and 25 parts deionized water are combined and gently heated under a nitrogen atmosphere. To this slurry is then added 2.75 parts of potassium bicarbonate, followed by 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, washed with water and saturated sodium chloride solution, 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 66.6% yield. gently heated under a nitrogen atmosphere The mixture is heated to reflux maintained the reaction mixture is extracted three times with 14 part portions of ethyl ether extracted six times with 25 parts by volume portions of dilute acetic acid solution again extracted with ethyl ether washed with water and saturated sodium chloride solution dried over anhydrous potassium carbonate Removal of the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 1.96 parts of piperidine is added 1.91 parts of potassium iodide and 25 parts deionized water under a nitrogen atmosphere. The mixture is gently warmed and 1.65 parts of potassium hydroxide and 7.51 parts of 2,2-diphenyl-4-bromobutyronitrile are added. The temperature is raised 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 four times with 25 parts by volume portions of a dilute acetic acid solution. The acid extracts are combined, neutralized to about pH 10 with 50% sodium hydroxide solution, and extracted again with ethyl ether. The ether extracts are combined, washed twice with 50 parts by volume portions of a saturated sodium chloride solution, and dried over anhydrous potassium carbonate. The solvent is removed under reduced pressure to afford, as an off-white solid, in 86.1% yield, 2,2-diphenyl-4-piperidinobutyronitrile. This compound melts at 74° - 77° C., and is represented by the following structural formula. ##STR16## The mixture is gently warmed The temperature is raised to reflux maintained the reaction mixture is extracted three times with 14 part portions of ethyl ether extracted four times with 25 parts by volume portions of a dilute acetic acid solution extracted again with ethyl ether washed twice with 50 parts by volume portions of a saturated sodium chloride solution dried over anhydrous potassium carbonate The solvent is removed under reduced pressure