p-Fluoronitrobenzene → 1-Isopropyl-4-(4-nitrophenyl)piperazine
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)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)C=O>[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
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a vial was added 4-fluoronitrobenzene (1.41 g, 1.06 mL, 0.01 mol), N,N-diisopropylethylamine (1.92 mL, 0.011 mmol), isopropylpiperazine (1.41 g, 0.011 mmol), and N,N-dimethylformamide (10 mL). Mixture was heated at 100° C. for 48 h in a sealed tube. The reaction mixture was cooled to room temperature and concentrated. The residue was purified via silica gel column chromatography (gradient elution with 0 to 10% methanol in dichloromethane) to afford 1-isopropyl-4-(4-nitrophenyl)piperazine.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated
- customThe residue was purified via silica gel column chromatography (gradient elution with 0 to 10% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-13d35c04055048c98e98cfd2b7d6949c
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557996B2
Reaction notes
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