Acetic Acid → 4-(4-Benzylpiperazinyl)1-phenylcyclohexanecarbonitrile

HRID 1491650Notes

Reaction equation

HRID 1491650 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)#[N:2].[CH2:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C.O>[CH2:16]([N:23]1[CH2:28][CH2:27][N:26]([CH:6]2[CH2:7][CH2:8][C:3]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)([C:1]#[N:2])[CH2:4][CH2:5]2)[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 759941-BenzylpiperazineHCID 912824-Oxo-1-phenylcyclohexanenitrileHCID 5003444Sodium cyanoborohydride

Product 1

HCID 540914944-(4-Benzylpiperazinyl)1-phenylcyclohexanecarbonitrileYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

35.0 g of 4-cyano-4-phenylcyclohexanone (0.176 mol), (prepared as disclosed in J. Amer. Chem. Soc. 74, (1972) 773) were dissolved with 31 g of 1-benzylpiperazine (0.176 mol) and 21 g of acetic acid in 200 ml of ethanol and, at room temperature, a solution of 12.5 g of sodium cyanoborohydride (0.19 mol) was slowly added dropwise. The mixture was stirred overnight, and then water was added and the mixture was extracted with dichloromethane. Drying and removal of the solvent by distillation resulted in a residue of 46.6 g (76%) of oil.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customDrying
  3. customremoval of the solvent
  4. distillationby distillation

Sources & evidence

ORD record
ord-f94a41dfadc847309d18fd2a95250074
Source dataset
uspto-grants-1994_12
Patent number
US05371088

Reaction notes

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