Reaktion #417972

ord-0b51cb84d1bd4441a423c8fd687574cc

Reaktionsgleichung

O
Water
O=[N+]([O-])c1ccc(Cl)c(OCCCBr)c1
compound 26a
O=[N+]([O-])c1ccc(Cl)c(OCCCBr)c1
2-(3-bromo-propoxy)-1-chloro-4-nitro benzene
c1ccc(N2CCNCC2)cc1
N-phenyl piperazine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=[N+]([O-])c1ccc(Cl)c(OCCCN2CCN(c3ccccc3)CC2)c1
title compound 26b
Ausbeute 78.0%
O=[N+]([O-])c1ccc(Cl)c(OCCCN2CCN(c3ccccc3)CC2)c1
1-[3-(2-chloro-5-nitro-phenoxy)-propyl]-4-phenyl-piperazine
Ausbeute 78.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeat room temperature
  2. 2
    Extraktionextracted with ethyl acetate (3×20 mL)
  3. 3
    TrocknenThe combined extracts were dried over sodium sulfate
  4. 4
    Einengenconcentrated under reduced pressure
  5. 5
    SonstigeThe crude product was purified by flash column chromatography

Vorschrift

To the compound 26a (2.1 g, 7.1 mmol) in DMF (9 mL) was added N-phenyl piperazine (1.16 g, 7.1 mmol) and potassium carbonate (1.28 g, 9.23 mmol). The mixture was stirred for 18 hrs. at room temperature. Water (10 mL) was added to the reaction mixture and extracted with ethyl acetate (3×20 mL). The combined extracts were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by flash column chromatography to get the title compound 26b in 78% yield as yellow solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08877752B2uspto-grants-2014_11