反应详情

After adding triethylamine (1.30 mL, 9.06 mmol) to a solution of 4-(5-methylpyridin-2-yl)aminopiperidine dihydrobromide (1.60 g, 4.53 mmol) in 1,2-dichloroethane (7 mL) and stirring the mixture for 30 minutes, a solution of (1-ethylcyclohexyl)acetaldehyde (1.54 g, 4.53 mmol) in 1,2-dichloroethane (8 mL) was added and the mixture was stirred for 15 minutes. Sodium triacetoxyborohydride (0.96 g, 4.53 mmol) was then added while cooling on ice, and after stirring the mixture for 5 minutes, it was further stirred at room temperature for 1 hour. A 25% aqueous ammonium chloride solution, chloroform and 3N aqueous sodium hydroxide were added to the reaction mixture, extraction was performed with chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100 g Merck Art. 9385, chloroform:methanol=95:5) to obtain the title compound as a brown oil (1.37 g, 4.16 mmol) (2 steps, 92% yield).

1. stirringthe mixture was stirred for 15 minutes
2. temperaturewhile cooling on ice
3. stirringafter stirring the mixture for 5 minutes
4. stirringit was further stirred at room temperature for 1 hour
5. washthe organic layer was washed with saturated aqueous sodium chloride
6. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe obtained residue was purified by silica gel column chromatography (100 g Merck Art. 9385, chloroform:methanol=95:5)