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

HRID 1921829Notes

Reaction equation

HRID 1921829 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[NH3:8].[CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:16][CH2:15]1)([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 780131-Isopropylpiperazine

Product 2

HCID 222AmmoniaHCID 98347891-Isopropyl-4-(4-nitrophenyl)piperazineYield 185.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-fluoronitrobenzene (5 g, 35.4 mmol) in THF (50 mL), 1-isopropylpiperazine (4.54 g, 35.4 mmol) and K2CO3 (7.35 g, 53.2 mmol) are added. The reaction mixture is stirred at room temperature overnight. The solvent is removed in vacuo and the residue is partitioned between EtOAc and water. The organic layer is washed with brine, dried over MgSO4, filtered and concentrated. The crude compound is purified by silica gel column chromatography using 99:1 and 98:2 DCM:NH3 (7M in MeOH) to give the title compound (8.2 g, 94%).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between EtOAc and water
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude compound is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-37694976a63b4dc2a6bbc7f9f295a34e
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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