Water → 4-(Piperazin-1-yl)benzonitrile

HRID 1767752Notes

Reaction equation

HRID 1767752 reaction equation
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.O>CS(C)=O>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:9][CH:10]=1)#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 27339954-(Piperazin-1-yl)benzonitrileYield 93.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

Potassium carbonate (20.7 g, 0.15 mol) was added to a solution of 4-fluorobenzonitrile (12.1 g, 0.1 mol) and piperazine (25.8 g, 0.3 mol) in dimethylsulfoxide (75 ml) and heated at 95° C. for 20 hours. The reaction was cooled and poured into water (1100 ml) and extracted into dichloromethane (4×400 ml). The organic solution was dried and the solvent removed in vacuo to yield 4-cyanophenylpiperazine (17.5 g, 93.6% yield):

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted into dichloromethane (4×400 ml)
  3. customThe organic solution was dried
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b5882785560547e3ac72fd05be61712a
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

Loading…