Reacción #1885021

ord-ea1ab50375b34e25b281175bbcaebf43

Ecuación de reacción

ClCc1ccc(Cl)nc1
2-chloro-5-chloromethylpyridine
NCC(F)F
2,2-difluoroethan-1-amine
CCN(CC)CC
triethylamine
FC(F)CNCc1ccc(Cl)nc1
N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethan-1-amine
Rendimiento 53.9%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ConcentraciónAfter concentrating the reaction mixture under reduced pressure, it
  2. 2
    Lavadowashed with ethyl acetate
  3. 3
    Extracciónextracted repeatedly with ethyl acetate
  4. 4
    ConcentraciónConcentrating the organic phase under reduced pressure

Procedimiento

At 45° C., 41.57 g (256.6 mmol) of 2-chloro-5-chloromethylpyridine, 20.80 g (256.6 mmol) of 2,2-difluoroethan-1-amine and 35.8 ml (256.6 mmol) of triethylamine are stirred in 500 ml of acetonitrile for 21 hours. After concentrating the reaction mixture under reduced pressure, it is taken up with 1 N aqueous hydrochloric acid and washed with ethyl acetate. The aqueous phase is alkalized with 2.5 N aqueous sodium hydroxide solution and extracted repeatedly with ethyl acetate. Concentrating the organic phase under reduced pressure affords 28.6 g (53% of theory) of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethan-1-amine.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08343893B2uspto-grants-2013_01