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

HRID 552385Notes

Reaction equation

HRID 552385 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 (5.00 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 under reduced pressure and the residue is partitioned between EtOAc and water. The organic layer is washed with brine, dried (MgSO4), filtered and the solvent is removed under reduced pressure. The crude compound is purified by silica gel column chromatography using 99:1 and 98:2 DCM:NH3 (7 M in MeOH) to give the title compound (8.2 g, 94%).

Workup

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

Sources & evidence

ORD record
ord-bae4142a09694c9b8273e0e26f33f1e3
Source dataset
uspto-grants-2011_05
Patent number
US07951818B2

Reaction notes

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