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

HRID 1164939Notes

Reaction equation

HRID 1164939 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 531671-Methylpiperazine

Product 1

HCID 28251981-Methyl-4-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 25.0 g (0.18 mol) of 1-fluoro-4-nitrobenzene and 19.5 g (0.2 mol) of 1-methylpiperazine in 300 mL of acetonitrile, add 48.9 g (0.35 mol) of anhydrous potassium carbonate. Heat the reaction mixture to 60° C. for 20 h under nitrogen. After this time, add 100 mL of water and concentrate mixture to 200 mL volume. Add another 100 mL of water and extract with 3×200 mL of methylene chloride. Extract the combined methylene chloride extracts with 100 mL of 6N hydrochloric acid solution and 3×200 mL of water. Make the combined aqueous extracts basic (pH=14) with 50% sodium hydroxide solution and extract with 3×200 mL of methylene chloride. Dry the extracts over anhydrous sodium sulfate. Remove the drying agent by filtration and evaporate the solvent in vacuo. Dissolve the residue in 150 mL of methanol and bubble hydrogen chloride gas through the solution until pH=1. Precipitate the product by addition of diethyl ether to obtain the title compound.

Workup

  1. concentrationconcentrate mixture to 200 mL volume
  2. additionAdd another 100 mL of water
  3. extractionextract with 3×200 mL of methylene chloride
  4. extractionExtract the combined methylene chloride
  5. extractionextract with 3×200 mL of methylene chloride
  6. dry with materialDry the extracts over anhydrous sodium sulfate
  7. customRemove the drying agent
  8. filtrationby filtration
  9. customevaporate the solvent in vacuo
  10. dissolutionDissolve the residue in 150 mL of methanol
  11. custombubble hydrogen chloride gas through the solution until pH=1
  12. customPrecipitate the product
  13. additionby addition of diethyl ether

Sources & evidence

ORD record
ord-86970fc83aeb4c7fac8ff8add14e48a0
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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