Réaction #417972

ord-0b51cb84d1bd4441a423c8fd687574cc

Équation de réaction

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
Rendement 78.0%
O=[N+]([O-])c1ccc(Cl)c(OCCCN2CCN(c3ccccc3)CC2)c1
1-[3-(2-chloro-5-nitro-phenoxy)-propyl]-4-phenyl-piperazine
Rendement 78.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autreat room temperature
  2. 2
    Extractionextracted with ethyl acetate (3×20 mL)
  3. 3
    SéchageThe combined extracts were dried over sodium sulfate
  4. 4
    Concentrationconcentrated under reduced pressure
  5. 5
    AutreThe crude product was purified by flash column chromatography

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08877752B2uspto-grants-2014_11