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

HRID 2083672Notes

Reaction equation

HRID 2083672 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 75.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. temperaturemaintained
  4. extractionthe reaction mixture is extracted three times with 14 part portions of ethyl ether
  5. extractionextracted six times with 25 parts by volume portions of dilute acetic acid solution
  6. extractionagain extracted with ethyl ether
  7. dry with materialdried over anhydrous potassium carbonate
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-f0824a4fd71640d1b36e68157487fe77
Source dataset
uspto-grants-1978_04
Patent number
US04086234

Reaction notes

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