反应详情

In 250 ml of 1,2-dichloroethane was dissolved 7.64 g of 1-benzoyl-2-(2-phenylethyl)-2-piperidinecarbonitrile. To this solution was added 8.0 g of aluminum chloride and the mixture was refluxed for 6 hours. The reaction mixture was then cooled and poured cautiously into 10% aqueous sodium hydroxide and extracted with methylene chloride and water. The methylene chloride layer was dried over anhydrous sodium sulfate and filtered and the solvent was distilled off. To the group was added 100 ml of methanol and 100 ml of 20% aqueous sodium hydroxide and the mixture was refluxed for 12 hours. After cooling, methanol was distilled off and the group was extracted with methylene chloride and water. The methylene chloride layer was dried over anhydrous sodium sulfate and filtered and the solvent was distilled off. The group was purified by alumina column chromatography using ethyl acetate-hexane (1:2) as the eluent. The active fraction was concentrated under reduced pressure and the group was treated with 6.0 ml of 4N-methanolic hydrochloric acid to give a solid. This solid was recrystallized from methylene chloride to provide 3.0 g of colorless crystals.

1. temperaturethe mixture was refluxed for 6 hours
2. temperatureThe reaction mixture was then cooled
3. extractionextracted with methylene chloride and water
4. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. distillationthe solvent was distilled off
7. additionTo the group was added 100 ml of methanol and 100 ml of 20% aqueous sodium hydroxide
8. temperaturethe mixture was refluxed for 12 hours
9. temperatureAfter cooling
10. distillationmethanol was distilled off
11. extractionthe group was extracted with methylene chloride and water
12. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
13. filtrationfiltered
14. distillationthe solvent was distilled off
15. customThe group was purified by alumina column chromatography
16. concentrationThe active fraction was concentrated under reduced pressure
17. additionthe group was treated with 6.0 ml of 4N-methanolic hydrochloric acid
18. customto give a solid
19. customThis solid was recrystallized from methylene chloride