反应 #452434

反应方程式

4-dimethylamino-1-cyclohexanone

4-benzyloxyphenylhydrazine hydrochloride

pyridine

→

title compound

收率 24.9%

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

收率 24.9%

溶剂

water

ethanol

water

反应条件

后处理

1. 1
   萃取the mixture extracted well with dichloromethane
2. 2
   干燥The combined organic extracts were dried over sodium sulfate
3. 3
   其他the volatiles removed under reduced pressure
4. 4
   洗涤eluting with 9:1 chloroform
5. 5
   浓缩concentrated under reduced pressure

实验过程

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.

来源