Réaction #452434

Équation de réaction

4-dimethylamino-1-cyclohexanone

4-benzyloxyphenylhydrazine hydrochloride

pyridine

→

title compound

Rendement 24.9%

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

Rendement 24.9%

Solvants

water

ethanol

water

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture extracted well with dichloromethane
2. 2
   SéchageThe combined organic extracts were dried over sodium sulfate
3. 3
   Autrethe volatiles removed under reduced pressure
4. 4
   Lavageeluting with 9:1 chloroform
5. 5
   Concentrationconcentrated under reduced pressure

Mode opératoire

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.

Source