Water → 1-Benzyl-4-(4-nitrophenyl)piperazine

HRID 479378Notes

Reaction equation

HRID 479378 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1.O>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 759941-Benzylpiperazine

Product 1

HCID 27474271-Benzyl-4-(4-nitrophenyl)piperazineYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Benzylpiperazine (2.8 ml; 16 mmol) and potassium carbonate (2.3 g; 17 mmol) were added to a solution of 1-chloro-4-nitrobenzene (2.0 g; 13 mmol) in dimethylformamide (0.5 ml), and the mixture was stirred for 7 hours in a bath controlled at 100° C. Water was added to the reaction mixture to conduct extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 2.9 g (yield: 76%) of 4-(4-benzyl-1-piperazinyl)-1-nitrobenzene as a colorless oil.

Workup

  1. customcontrolled at 100° C
  2. extractionextraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a06b0b315d3441e6a2b53be2ed8f3193
Source dataset
uspto-grants-2003_11
Patent number
US06645957B2

Reaction notes

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