Piperazine → 1-(2,4-Dichlorophenyl)piperazine

HRID 270764

Reaktionsgleichung

Reaktionsgleichung von HRID 270764
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+].[NH:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1.[Cl:59][C:60]1[CH:65]=[C:64]([Cl:66])[CH:63]=[CH:62][C:61]=1Br>C1COCC1>[Cl:59][C:60]1[CH:65]=[C:64]([Cl:66])[CH:63]=[CH:62][C:61]=1[N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1

Komponenten

6

Edukt 4

HCID 4837PiperazineHCID 709471-Bromo-2,4-dichlorobenzeneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Produkt 1

HCID 27375271-(2,4-Dichlorophenyl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

BINAP (219 mg), Pd(II) acetate (397 mg, 0.176 mmol), tBuONa (1.19 g, 12.3 mmol), piperazine (837 mg, 9.73 mmol) and THF (40 mL) were mixed together and stirred at room temperature for 30 min under nitrogen atmosphere. 2,4-dichlorobromobenzene (2 g, 8.84 mmol) in THF (10 mL) was added to the mixture drop wise and heated at 70° C. for 14 h. Excess THF was then evaporated and extracted with ethyl acetate. The crude product was obtained on concentration of the ethyl acetate layer after washing with brine and drying. Flash chromatography on silica gel eluting with 2% MeOH in CHCl3 gave 1-(2,4-Dichloro-phenyl)-piperazine.

Aufarbeitung

  1. temperatureheated at 70° C. for 14 h
  2. customExcess THF was then evaporated
  3. extractionextracted with ethyl acetate
  4. customThe crude product was obtained on concentration of the ethyl acetate layer
  5. washafter washing with brine
  6. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-b76be913381d43bbaac68cb899eb6723
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449576B1

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