Reacción #171403

Ecuación de reacción

1-bromo-4-(3-bromopropoxy)benzene

4,4-difluoropiperidine hydrochloride

potassium carbonate

→

title compound

Rendimiento 50.9%

1-[3-(4-bromophenoxy)propyl]-4,4-difluoropiperidine

Rendimiento 50.9%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated in vacuo
2. 2
   OtroThe residue was partitioned between ether and saturated aqueous sodium bicarbonate
3. 3
   OtroThe layers were separated
4. 4
   Lavadothe organic layer was washed with saturated aqueous sodium bicarbonate, water and brine
5. 5
   SecadoThe organic layer was dried (Na2SO4)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroPurification by flash column chromatography on an analogix SF40-80g column (hexanes/ethyl acetate=7:3)

Procedimiento

A suspension of 1-bromo-4-(3-bromopropoxy)benzene (1.85 g, 6.29 mmol), 4,4-difluoropiperidine hydrochloride (1.0 g, 6.34 mmol) and potassium carbonate (2.17 g, 15.7 mmol) in acetonitrile (100 mL) was heated to 60° C. overnight, then concentrated in vacuo. The residue was partitioned between ether and saturated aqueous sodium bicarbonate. The layers were separated; the organic layer was washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography on an analogix SF40-80g column (hexanes/ethyl acetate=7:3) afforded the title compound as a clear oil (1.07 g, 50%). LCMS m/z 334.3 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.90-2.08 (m, 6 H) 2.47-2.64 (m, 6 H) 3.99 (t, J=6.34 Hz, 2 H) 6.75-6.81 (m, 2 H) 7.34-7.40 (m, 2 H).

Fuente