1-Bromo-4-nitrobenzene → 1-Ethyl-4-(4-nitrophenyl)piperazine

HRID 43051

Reaktionsgleichung

Reaktionsgleichung von HRID 43051
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[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:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15][CH2:14]1)[CH3:12]

Komponenten

5

Edukt 2

HCID 114661-Bromo-4-nitrobenzeneHCID 791961-Ethylpiperazine

Produkt 1

HCID 28575491-Ethyl-4-(4-nitrophenyl)piperazineAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1-bromo-4-nitrobenzene (6 g, 29.7 mmol) and 1-ethylpiperazine (7.6 mL, 59.4 mmol, 2 equiv) was heated to 80° C. for 15 h. After cooling to rt, the reaction mixture was diluted with H2O and DCM/MeOH (9:1, v/v). The aqueous layer was separated and extracted with DCM/MeOH, 9:1. The organic phase was washed with brine, dried (sodium sulfate), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1) afforded 6.2 g of the title compound as a yellow solid: ESI-MS: 236.0 [M+H]+; tR=2.35 min (purity: 100%, system 1); TLC: Rf=0.50 (DCM/MeOH+1% NH3aq, 9:1).

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. customThe aqueous layer was separated
  3. extractionextracted with DCM/MeOH, 9:1
  4. washThe organic phase was washed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-5b6ff8a8bd58471581117686941e66c0
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536175B2

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