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

HRID 2236578Notes

Reaction equation

HRID 2236578 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+]>CN(C=O)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

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 531671-Methylpiperazine

Product 1

HCID 28251981-Methyl-4-(4-nitrophenyl)piperazineYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Fluoro-4-nitro-benzene (1.00 g, 7.09 mmol) is dissolved in DMF (20 mL), and to this solution, is added 1-methyl-piperazine (0.944 mL, 8.51 mmol) followed by K2CO3 (1.47 g, 10.6 mmol). After stirring the mixture at rt for 18 h, the solvent is removed via high vacuum. The resulting residue is dissolved in EtOAc (100 mL) and washed with H2O (10 mL) and brine (10 mL) and then dried (Na2SO4). The solvent is taken off via high vacuum to afford the product as a solid (1.50 g, 96%); 1H NMR (DMSO-d6) δ 2.17 (s, 3H), 2.37-2.42 (m, 4H), 3.39-3.43 (m, 4H), 6.98 (d, J=9.6 Hz, 2H), 8.00 (d, J=9.5 Hz, 2H); mass spectrum [(+) ESI], m/z 222 (M+H)+.

Workup

  1. customthe solvent is removed via high vacuum
  2. dissolutionThe resulting residue is dissolved in EtOAc (100 mL)
  3. washwashed with H2O (10 mL) and brine (10 mL)
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-e97ad2ec5a4d4e1f83d2d64cacf78bdf
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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