Potassium Cyanide → 1-Benzyl-4-(cyanomethyl)piperidine-4-carbonitrile

HRID 491461Notes

Reaction equation

HRID 491461 reaction equation
C(OC(=O)[C:5](=[C:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:6]#[N:7])C.[C-:22]#[N:23].[K+]>CCO.O>[CH2:14]([N:11]1[CH2:10][CH2:9][C:8]([CH2:5][C:6]#[N:7])([C:22]#[N:23])[CH2:13][CH2:12]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 424752Ethyl 2-(1-benzylpiperidin-4-ylidene)-2-cyanoacetate

Product 1

HCID 128476541-Benzyl-4-(cyanomethyl)piperidine-4-carbonitrileYield 81.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of (1-benzyl-piperidin-4-ylidene)-cyano-acetic acid ethyl ester (112.9 g, 0.40 mol) in EtOH (500 ml) and H2O (100 ml), potassium cyanide (64.6 g, 0.99 mol) is added at ambient temperature. The reaction mixture is stirred at 65 C.° for 24 h. After removal of EtOH, H2O is added to the residue. The waster phase is extracted with diethyl ether. The combined extracts are washed with H2O and brine, dried over sodium sulfate and evaporated down to give 77.7 g of 1-benzyl-4-cyanomethyl-piperidine-4-carbonitrile.

Workup

  1. customAfter removal of EtOH, H2O
  2. additionis added to the residue
  3. extractionThe waster phase is extracted with diethyl ether
  4. washThe combined extracts are washed with H2O and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated down

Sources & evidence

ORD record
ord-dab84b2fcf074c6bb6a68688472e8a72
Source dataset
uspto-grants-2009_05
Patent number
US07531546B2

Reaction notes

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