反应详情

The N-(4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide acetate (3.71 g, 10.0 mmol), 6-methyl-2-vinylpyridine (1.43 g, 12.0 mmol ) and sodium acetate (0.82 g) were dissolved in a mixture comprising methanol (20 ml) and water (20 ml). The obtained solution was heated under reflux for 5 hours, followed by the addition of sodium hydroxide (3.20 g). The obtained mixture was heated under reflux for additional three hours and acidified with 2N aqueous hydrochloric acid. The pH of the mixture was adjusted to about 8 with an aqueous solution of sodium hydrogencarbonate. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of common salt, dried over magnesium sulfate and concentrated. The obtained oily residue was purified by column chromatography (chloroform:methanol:aqueous ammonia=90:9:1) and recrystallized from ethyl acetate/ether to give the title compound as a white crystal (2.71 g, overall yield of two steps: 70%).

1. temperatureThe obtained solution was heated
2. temperatureunder reflux for 5 hours
3. temperatureThe obtained mixture was heated
4. temperatureunder reflux for additional three hours
5. extractionThe resulting mixture was extracted with ethyl acetate
6. washThe organic layer was washed with water
7. dry with materiala saturated aqueous solution of common salt, dried over magnesium sulfate
8. concentrationconcentrated
9. customThe obtained oily residue was purified by column chromatography (chloroform:methanol:aqueous ammonia=90:9:1)
10. customrecrystallized from ethyl acetate/ether