Piperazine → 1-(2-Nitrophenyl)piperazine

HRID 2395737Notes

Reaction equation

HRID 2395737 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21]>C(#N)C.C(Cl)Cl>[N+:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 4837PiperazineHCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 1009491-(2-Nitrophenyl)piperazine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Piperazine (24.46 g) is dissolved in acetonitrile (200 ml) and anhydrous potassium carbonate (10.47 g) is added. Then 2-chloronitrobenzene (10.0 g) is added dropwise. After stirring 1 hr at 20°, the reaction mixture is diluted with methylene chloride, washed with water, and saturated aqueous potassium carbonate. After drying over anhydrous sodium sulfate, the reaction mixture is concentrated under reduced pressure to give the title compound, NMR (300 MHz, CDCl3) 7.75, 7.49, 7.14, 7.04, 3.03 and 1.93 δ.

Workup

  1. washwashed with water, and saturated aqueous potassium carbonate
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. concentrationthe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-51cecae43ee0493b86e43932a3c9668f
Source dataset
uspto-grants-1996_02
Patent number
US05489593

Reaction notes

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