Water → N-(2-Cyanophenyl)piperazine

HRID 612415Notes

Reaction equation

HRID 612415 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[N:1]1([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 11430Potassium CarbonateHCID 678552-Fluorobenzonitrile

Product 1

HCID 2735875N-(2-Cyanophenyl)piperazineYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Piperazine (6.0 g, 69 mmol) was dissolved in dimethylsulfoxide (50 ml), 2-fluorobenzonitrile (0.95 ml, 9 mmol) and potassium carbonate (2.2 g, 17 mmol) were added and the mixture was stirred at room temperature for 16 h. Water (100 ml) was added and the mixture was extracted with toluene (2×100 ml). The combined organic extracts were washed with 1 N sodium hydroxide (3×75 ml), dried (MgSO4) and concentrated in vacuo to give 1.48 g (88%) 2-(1-piperazinyl)benzonitrile as an oil.

Workup

  1. extractionthe mixture was extracted with toluene (2×100 ml)
  2. washThe combined organic extracts were washed with 1 N sodium hydroxide (3×75 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e52d3689ac74100a695aa63cc96a2e1
Source dataset
uspto-grants-1999_12
Patent number
US06004961

Reaction notes

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