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

HRID 714984Notes

Reaction equation

HRID 714984 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.F[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 531671-Methylpiperazine

Product 1

HCID 28251981-Methyl-4-(4-nitrophenyl)piperazineYield 85.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-methylpiperazine (0.605 ml, 5.45 mmol) in DMF (6.25 ml) was added 4-fluoronitrobenzene (0.750 ml, 7.07 mmol) and potassium carbonate (1.13 g, 8.18 mmol) and the reaction mixture stirred at 90° C. overnight. The reaction was then cooled to room temperature, diluted with DCM and washed with water. The organic phase was dried over MgSO4 and the solvent removed in vacuo. The residue was purified by silica gel silica chromatography using a 0-10% MeOH in DCM gradient to afford 1-methyl-4-(4-nitrophenyl)piperazine (1.03 g, 4.66 mmol, 85%) as a yellow solid. 1H NMR (DMSO) δ 2.37 (3H, s), 2.58 (4H, t), 3.45 (4H, t), 6.82 (2H, d), 8.12 (2H, d). LCMS (1) Rt: 1.63 min; m/z (ES+) 222.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic phase was dried over MgSO4
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by silica gel silica chromatography

Sources & evidence

ORD record
ord-f90560cc2f1d4378b986f9ebcc6edf28
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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