1-Fluoro-3-nitrobenzene → 1-Ethyl-4-(3-nitrophenyl)piperazine

HRID 2066692Notes

Reaction equation

HRID 2066692 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[CH2:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH3:12]>O.C(Cl)Cl.CO>[CH2:11]([N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=2)[CH2:15][CH2:14]1)[CH3:12]

Participants

5

Reactant 2

HCID 98231-Fluoro-3-nitrobenzeneHCID 791961-Ethylpiperazine

Product 1

HCID 582359851-Ethyl-4-(3-nitrophenyl)piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 1-fluoro-3-nitrobenzene (3.2 mL, 29.7 mmol) and N-ethyl-piperazine (7.6 mL, 59.4 mmol, 2 equiv) is heated to reflux and stirred for 117 h. The reaction mixture is allowed to cool to RT and diluted with H2O (40 mL) and DCM/MeOH (9:1, 80 mL). The aqueous layer is separated and extracted with DCM/MeOH (9:1). The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the crude product by silica gel column chromatography (DCM/MeOH, 1:0-95:5) affords the title compound as a brown oil: ESI-MS: 236.0 [MH]+; tR=2.49 min (purity: 99%, system 1); TLC: Rf=0.26 (DCM/MeOH, 95:5).

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. customThe aqueous layer is separated
  4. extractionextracted with DCM/MeOH (9:1)
  5. washThe organic phase is washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the crude product by silica gel column chromatography (DCM/MeOH, 1:0-95:5)

Sources & evidence

ORD record
ord-9589bc078a594381a18a2857b7901f29
Source dataset
uspto-grants-2012_10
Patent number
US08293746B2

Reaction notes

Loading…