反应详情

A mixture of 1-acetyl-N-(quinolin-8-yl)-4-piperidinecarboxamide (51.28 g), glacial acetic acid (800 ml), and platinum oxide (4.00 g) was shaken under hydrogen at ambient temperature until the calculated amount of hydrogen was consumed. The platinum oxide was filtered through a bed of celite and the filter cake was washed with acetic acid. The filtrate was evaporated to ~200 ml, and was then stirred under reflux for four hrs, basified with 10% ammonium hydroxide solution and extracted with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was combined with material from another reaction mixture. The combined residue was purified by high performance liquid chromatography (silica gel; 20:1 dichloromethane-methanol). The appropriate fractions were collected and evaporated. The residue was crystallized from ethyl acetate and then recrystallized from ethyl acetate to give 50.2 g (76%) of product, mp 139°-140° C.

1. customwas consumed
2. filtrationThe platinum oxide was filtered through a bed of celite
3. washthe filter cake was washed with acetic acid
4. customThe filtrate was evaporated to ~200 ml
5. temperatureunder reflux for four hrs
6. extractionextracted with dichloromethane
7. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationthe filtrate was concentrated
10. customThe combined residue was purified by high performance liquid chromatography (silica gel; 20:1 dichloromethane-methanol)
11. customThe appropriate fractions were collected
12. customevaporated
13. customThe residue was crystallized from ethyl acetate
14. customrecrystallized from ethyl acetate