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

HRID 271127Notes

Reaction equation

HRID 271127 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>CS(C)=O>[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

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 531671-Methylpiperazine

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1-fluoro-4-nitrobenzene (2.54 mL, 24 mmol) and N-methylpiperazine (2.22 mL, 20 mmol) was dissolved in DMSO (25 mL) and irradiated in a microwave oven (max power 250 W, 160° C.) for 10 min, then cooled to room temperature. The solvent was removed under high vacuum, and the residue was dissolved in EtOAc and extracted with 0.5M aqueous HCl. The aqueous extracts were combined, basified to pH 8, and extracted with EtOAc. The organic layer was washed with brine, and then dried over MgSO4. Evaporation of the solvent provided the crude 1-methyl-4-(4-nitrophenyl)piperazine as an brown oil.

Workup

  1. customirradiated in a microwave oven (max power 250 W, 160° C.) for 10 min
  2. customThe solvent was removed under high vacuum
  3. dissolutionthe residue was dissolved in EtOAc
  4. extractionextracted with 0.5M aqueous HCl
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f7f4af4ecf7d49978c36d2a04c4d7401
Source dataset
uspto-grants-2008_11
Patent number
US07452887B2

Reaction notes

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