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

HRID 2083671Notes

Reaction equation

HRID 2083671 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[I-].[K+].C(=O)(O)[O-].[K+].[C:14]1([C:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:23][CH2:24]Br)[C:21]#[N:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[C:26]1([C:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([CH2:23][CH2:24][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:21]#[N:22])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8082PiperidineHCID 965754-Bromo-2,2-diphenylbutyronitrileHCID 516893Potassium Bicarbonate

Product 1

HCID 2245772,2-Diphenyl-4-piperidin-1-ylbutanenitrileYield 66.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. temperaturegently heated under a nitrogen atmosphere
  2. temperatureThe mixture is heated
  3. temperatureto reflux
  4. temperaturemaintained
  5. extractionthe reaction mixture is extracted three times with 14 part portions of ethyl ether
  6. extractionextracted six times with 25 parts by volume portions of dilute acetic acid solution
  7. extractionagain extracted with ethyl ether
  8. washwashed with water and saturated sodium chloride solution
  9. dry with materialdried over anhydrous potassium carbonate
  10. customRemoval of the solvent

Sources & evidence

ORD record
ord-ac663a5a1f92405a993d0944f95d3bf9
Source dataset
uspto-grants-1978_04
Patent number
US04086234

Reaction notes

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