반응 #310438

반응 방정식

3-phenylsulfonylpropylindole

6-fluoro-3-(4-piperidyl)-1,2-benzisoxazole hydrochloride

potassium carbonate

2-butanone

→

product

수율 31.5%

3-{3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidyl]propyl}-2-methylindole

수율 31.5%

용매

water

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux for 24 hrs
3. 3
   추출the aqueous mixture was extracted with dichloromethane
4. 4
   추출The organic extract
5. 5
   세척was washed with water
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   기타the solvent was removed under reduced pressure
8. 8
   기타The resultant oil was triturated with isopropyl ether
9. 9
   기타the solid was collected
10. 10
    기타the combined sample was chromatographed on 100 g silica gel
11. 11
    기타The eluent was evaporated
12. 12
    workup.DISSOLUTIONthe solid was dissolved in 125 ml toluene
13. 13
    workup.ADDITIONa saturated hydrogen chloride-toluene solution was added until no more precipitate
14. 14
    기타formed
15. 15
    여과The precipitate was filtered
16. 16
    기타dried
17. 17
    기타Recrystallization from acetone

실험 절차

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°.

출처