Reacción #567376

Ecuación de reacción

sodium cyanoborohydride

(2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde

dichloroethane acetic acid

(diethylamino)ethylamine

sodium bicarbonate

→

title compound

Rendimiento 30.1%

(2R,5S)-2-{4-Chloro-2-[(2-diethylamino-ethylamino)-methyl]-phenoxy}-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone

Rendimiento 30.1%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction was stirred overnight at ambient temperature
2. 2
   ExtracciónThe product was extracted with dichloromethane (2×) and diethyl ether (2×)
3. 3
   SecadoThe combined organics were dried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo

Procedimiento

To a solution of (2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde (0.100 g, 0.25 mmol) in 10:1 dichloroethane acetic acid (2.2 mL) was added (diethylamino)ethylamine (0.088 mL, 0.625 mmol) and the resulting solution was stirred for 1 hour at ambient temperature. To this was added sodium cyanoborohydride (0.0094 g, 0.15 mmol) and the reaction was stirred overnight at ambient temperature. Upon completion water was added and the mixture was basified with solid sodium bicarbonate (pH>10). The product was extracted with dichloromethane (2×) and diethyl ether (2×). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.039 g, x 30% yield)

Fuente