Reacción #452434

Ecuación de reacción

4-dimethylamino-1-cyclohexanone

4-benzyloxyphenylhydrazine hydrochloride

pyridine

→

title compound

Rendimiento 24.9%

6-benzyloxy-3-dimethylamino-1,2,3,4-tetrahydrocarbazole

Rendimiento 24.9%

Disolventes

water

ethanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture extracted well with dichloromethane
2. 2
   SecadoThe combined organic extracts were dried over sodium sulfate
3. 3
   Otrothe volatiles removed under reduced pressure
4. 4
   Lavadoeluting with 9:1 chloroform
5. 5
   Concentraciónconcentrated under reduced pressure

Procedimiento

To a solution of 3.78 gm (26.8 mMol) 4-dimethylamino-1-cyclohexanone and 6.69 gm (26.8 mMol) 4-benzyloxyphenylhydrazine hydrochloride in 50 mL ethanol were added 2.17 mL (26.8 mMol) pyridine. To this solution were added 5×10 mL portions of water and the reaction mixture then stored at 0° C. for 18 hours. The reaction mixture was then diluted with an additional 50 mL of water and the mixture extracted well with dichloromethane. The combined organic extracts were dried over sodium sulfate and the volatiles removed under reduced pressure. The residual oil was subjected to flash silica gel chromatography, eluting with 9:1 chloroform:methanol. Fractions shown to contain the desired product were combined and concentrated under reduced pressure to give 2.14 gm (24.9%) of the title compound.

Fuente