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

HRID 1164938Notes

Reaction equation

HRID 1164938 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:21]2[CH2:22][CH2:23][N:18]([CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:19][CH2:20]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 759941-Benzylpiperazine

Product 1

HCID 27474271-Benzyl-4-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 48.67 g (0.35 mol) of 1-fluoro-4-nitrobenzene and 67.15 g (0.38 mol) of 1-benzylpiperazine in 600 mL of acetonitrile, add 52.65 g (0.381 mol) of anhydrous potassium carbonate. Heat the reaction mixture to reflux for 20h under nitrogen. After this time, add 300 mL of water and concentrate mixture to 500 mL volume. Extract the mixture with 3×500 mL of methylene chloride. Remove the solvent of the combined organic layers in vacuo. Triturate the resulting crystalline residue with 1000 mL of diethyl ether and filter to obtain title compound.

Workup

  1. temperatureHeat the reaction mixture
  2. concentrationconcentrate mixture to 500 mL volume
  3. extractionExtract the mixture with 3×500 mL of methylene chloride
  4. customRemove the solvent of the combined organic layers in vacuo
  5. customTriturate the resulting crystalline residue with 1000 mL of diethyl ether
  6. filtrationfilter

Sources & evidence

ORD record
ord-ced0dc05a9aa48ae9be71c48018018c6
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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