p-Fluoronitrobenzene → 1-Tert-butyl-4-(4-nitrophenyl)piperazine

HRID 1783991Notes

Reaction equation

HRID 1783991 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[NH3:8].[C:11]([N:15]1[CH2:20][CH2:19][N:18]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:17][CH2:16]1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 35305721-Tert-butylpiperazine

Product 2

HCID 222AmmoniaHCID 574441581-Tert-butyl-4-(4-nitrophenyl)piperazineYield 118.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 1-fluoro-4-nitro-benzene (314 mg, 2.23 mmol) and 4-tert-butyl-piperazine (1 g, 3.34 mmol) in dioxane (15 mL) is added K2CO3 (1.65 mg, 11.9 mmol) and the reaction is stirred at 130° C. overnight. The solvent is evaporated under vacuum and the residue is partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over MgSO4, filtered and concentrated to give a crude compound. Purification by silica gel column chromatography eluting with DCM followed by 99:1 DCM:NH3 (7M in MeOH) affords the title compound (348 mg, 55.4%). LCMS: Rt 3.87 min (99%).

Workup

  1. customThe solvent is evaporated under vacuum
  2. customthe residue is partitioned between ethyl acetate and water
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude compound
  8. customPurification by silica gel column chromatography
  9. washeluting with DCM

Sources & evidence

ORD record
ord-3854d07172e940f88e508a0d34f2519e
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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