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

HRID 1783979Notes

Reaction equation

HRID 1783979 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-e652935c29cc4a9a9e672a5a24d1ecaa
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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