反应详情

A stirred mixture of 3.1 g of 2-methyl-3-(3-phenylsulfonylpropylindole, 2.1 g of 6-fluoro-3-(4-piperidyl)-1,2-benzisoxazole hydrochloride, 6.3 g of potassium carbonate and 50 ml of 2-butanone was heated under reflux for 24 hrs. The reaction mixture was poured into water and the aqueous mixture was extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The resultant oil was triturated with isopropyl ether and the solid was collected. The solid was combined with a 1.6 g sample of previously prepared material and the combined sample was chromatographed on 100 g silica gel, using 2% methanol-chloroform as eluent. The eluent was evaporated and the solid was dissolved in 125 ml toluene and a saturated hydrogen chloride-toluene solution was added until no more precipitate formed. The precipitate was filtered and dried. Recrystallization from acetone afforded 2.7 g (31.5%) of product, mp 208°-210°.

1. temperaturewas heated
2. temperatureunder reflux for 24 hrs
3. extractionthe aqueous mixture was extracted with dichloromethane
4. extractionThe organic extract
5. washwas washed with water
6. dry with materialdried over anhydrous magnesium sulfate
7. customthe solvent was removed under reduced pressure
8. customThe resultant oil was triturated with isopropyl ether
9. customthe solid was collected
10. customthe combined sample was chromatographed on 100 g silica gel
11. customThe eluent was evaporated
12. dissolutionthe solid was dissolved in 125 ml toluene
13. additiona saturated hydrogen chloride-toluene solution was added until no more precipitate
14. customformed
15. filtrationThe precipitate was filtered
16. customdried
17. customRecrystallization from acetone