p-Fluoronitrobenzene → 1-Benzyl-4-(4-nitrophenyl)piperazine

HRID 1292980Notes

Reaction equation

HRID 1292980 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.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 759941-Benzylpiperazine

Product 1

HCID 27474271-Benzyl-4-(4-nitrophenyl)piperazineYield 57%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 1-benzylpiperazine (8.81 g, 50.0 mmol), 4-fluoronitrobenzene (5.31 mL, 50.0 mmol), and K2CO3 (6.90 g, 50.0 mmol) in ethanol is heated at reflux temperature under nitrogen for 18 h, cooled, diluted with water, and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo to give a solid residue. The solid is triturated with 20:80 ethyl acetate:hexanes and filtered. The filtercake is air-dried to afford the title compound as orange crystals, 8.45 g (57% yield), mp 218–219° C., characterized by NMR and mass spectral analyses.

Workup

  1. temperatureat reflux temperature under nitrogen for 18 h
  2. temperaturecooled
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined extracts are dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a solid residue
  7. customThe solid is triturated with 20:80 ethyl acetate
  8. filtrationhexanes and filtered
  9. customThe filtercake is air-dried

Sources & evidence

ORD record
ord-f1e1736b027b4efa9e8f9081d3867e14
Source dataset
uspto-grants-2007_07
Patent number
US07238696B2

Reaction notes

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