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

HRID 2115876Notes

Reaction equation

HRID 2115876 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH:20]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([CH3:22])[CH3:21]>CN(C=O)C>[CH:20]([N:23]1[CH2:28][CH2:27][N:26]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:25][CH2:24]1)([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 780131-IsopropylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 98347891-Isopropyl-4-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a vial was added 4-fluoronitrobenzene (1.41 g, 1.06 mL, 0.01 mol), DIEA (1.92 mL, 0.011 mmol), isopropylpiperazine (1.41 g, 0.011 mmol), and DMF (10 mL). Mixture was heated at 100° C. for 48 h in a sealed tube. The reaction mixture was cooled to RT and concentrated. The residue was purified via silica gel column chromatography (gradient elution with 0 to 10% MeOH in DCM) to afford 1-isopropyl-4-(4-nitrophenyl)piperazine.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. concentrationconcentrated
  3. customThe residue was purified via silica gel column chromatography (gradient elution with 0 to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-fbe907bec9ca4252adf69352093fa457
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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