반응 #83870

반응 방정식

6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole

K2CO3

4-(3-bromopropoxy)-3-methoxybenzamide

→

4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzamide

수율 64.3%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux for 5 hours
3. 3
   기타At the end of the reaction the solvent
4. 4
   기타was evaporated
5. 5
   추출The residue was extracted into dichloromethane
6. 6
   여과The inorganic insolubles were filtered off
7. 7
   농축The dichloromethane was concentrated again
8. 8
   기타The crude residue was purified by flash chromatography over a silica gel column (55 g, SiO2 ; eluted with 1% methanol in dichloromethane, 1l; 2% methanol in dichloromethane, 1 )
9. 9
   기타The material thus obtained
10. 10
    기타Recrystallization from hot ethanol (60 ml)

실험 절차

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.2 g, 10.0 mmol), K2CO3 (2.0 g) and 4-(3-bromopropoxy)-3-methoxybenzamide (2.32 g, 8.0 mmol) in acetonitrile (80 ml) was heated at reflux for 5 hours. At the end of the reaction the solvent was evaporated. The residue was extracted into dichloromethane. The inorganic insolubles were filtered off. The dichloromethane was concentrated again. The crude residue was purified by flash chromatography over a silica gel column (55 g, SiO2 ; eluted with 1% methanol in dichloromethane, 1l; 2% methanol in dichloromethane, 1 ). The material thus obtained weighed 2.93 g (84%) as white crystals. Recrystallization from hot ethanol (60 ml) gave 2.2 g of 4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzamide as white crystals, m.p.=163°-164° C.

출처