Piperazine → 1-Phenyl-4-piperazin-1-yl-cyclohexanecarbonitrile

HRID 1167720Notes

Reaction equation

HRID 1167720 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].[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1.CCO.CCOC(C)=O.CO.CCOC(C)=O>[C:10]1([C:3]2([C:1]#[N:2])[CH2:8][CH2:7][CH:6]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[CH2:5][CH2:4]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

9

Reactant 4

HCID 4837PiperazineHCID 6101p-Toluenesulfonic acidHCID 912824-Oxo-1-phenylcyclohexanenitrileHCID 4311764Sodium borohydride

Product 1

HCID 229934561-Phenyl-4-piperazin-1-yl-cyclohexanecarbonitrileYield 40.2%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 4-cyano-4-phenyl-cyclohexanone (0.23 g, 1.2 mmol) and piperazine (0.30 g, 3.5 mmol) in 20 ml of toluene was stirred at reflux for 2 h in presence of catalytic amount of p-toluenesulfonic acid. The reaction mixture was concentrated in vacuo to provide a white solid, which was redissolved in 20 ml of EtOH and stirred with NaBH4 (0.30 g, 80 mmol) for 12 h at 25° C. Reaction mixture was diluted with 100 ml of EtOAc and washed with brine several times. Organic layer was dried over MgSO4 and concentrated in vacuo, to provide oily residue, which was subjected to column chromatography (10% MeOH/EtOAc) to yield 0.13 g (40%) of the desired product as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto provide a white solid, which
  3. customReaction mixture
  4. washwashed with brine several times
  5. dry with materialOrganic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto provide oily residue, which

Sources & evidence

ORD record
ord-211fa3c26dfc4e46a0efeaf82d43ebfe
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

Loading…