Reacción #417972

ord-0b51cb84d1bd4441a423c8fd687574cc

Ecuación de reacción

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

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroat room temperature
  2. 2
    Extracciónextracted with ethyl acetate (3×20 mL)
  3. 3
    SecadoThe combined extracts were dried over sodium sulfate
  4. 4
    Concentraciónconcentrated under reduced pressure
  5. 5
    OtroThe crude product was purified by flash column chromatography

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08877752B2uspto-grants-2014_11