反応 #452434

反応方程式

4-dimethylamino-1-cyclohexanone

4-benzyloxyphenylhydrazine hydrochloride

pyridine

→

title compound

収率 24.9%

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

収率 24.9%

溶媒

water

ethanol

water

反応条件

後処理

1. 1
   抽出the mixture extracted well with dichloromethane
2. 2
   乾燥The combined organic extracts were dried over sodium sulfate
3. 3
   その他the volatiles removed under reduced pressure
4. 4
   洗浄eluting with 9:1 chloroform
5. 5
   濃縮concentrated under reduced pressure

実験手順

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.

出典