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

HRID 43052

Reaktionsgleichung

Reaktionsgleichung von HRID 43052
F[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][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:3]=[CH:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=2)[CH2:15][CH2:14]1)[CH3:12]

Komponenten

5

Edukt 2

HCID 98231-Fluoro-3-nitrobenzeneHCID 791961-Ethylpiperazine

Produkt 1

HCID 582359851-Ethyl-4-(3-nitrophenyl)piperazineAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

A mixture of 2-fluoro-4-nitrobenzene (3.2 mL, 29.7 mmol) and 1-ethylpiperazine (7.6 mL, 59.4 mmol, 2 equiv) was heated to reflux for 117 h. After cooling to rt, the reaction mixture was diluted with H2O and DCM/MeOH, 9:1. The aqueous layer was separated and extracted with DCM/MeOH, 9:1. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/MeOH, 1:0→95:5) afforded 6 g of the title compound as a brown oil: ESI-MS: 236.0 [M+H]+; tR=2.49 min (System 1); TLC: Rf=0.26 (DCM/MeOH, 95:5).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 117 h
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM/MeOH, 9:1
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the residue by silica gel column chromatography (DCM/MeOH, 1:0→95:5)

Quellen und Nachweise

ORD-Eintrag
ord-9fb70e2a006546babb2dbf95ec279807
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536175B2

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