반응 #83862

반응 방정식

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

K2CO3

1-[4-(3-bromopropoxy)-3,5-dibromophenyl]ethanone

→

1-[3,5-dibromo-4-[3-[4-(6-fluoro-1,2- benzisoxazol-3-yl)-1-piperidinyl]propoxy]-phenyl]ethanone

수율 58.7%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux for 3 hours
3. 3
   기타At the end of the reaction
4. 4
   기타the solvent was evaporated
5. 5
   추출the residue was extracted into dichloromethane (150 ml)
6. 6
   여과The insolubles were filtered off
7. 7
   농축The dichloromethane solution was concentrated down to an oil
8. 8
   기타The purification
9. 9
   세척was done by flash chromatography on a silica gel column (SiO2, 47 g; eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 600 ml)
10. 10
    기타The material thus purified as a colorless oil
11. 11
    기타Recrystallization from ethanol

실험 절차

A stirred mixture of 6-fluoro-3-(4-piperidinyl)1,2-benzisoxazole (2.0 g, 9.0 mmol), K2CO3 (1.3 g), and 1-[4-(3-bromopropoxy)-3,5-dibromophenyl]ethanone (2.65 g, 9.0 mmol) and acetonitrile (50 ml) was heated at reflux for 3 hours. At the end of the reaction, the solvent was evaporated and the residue was extracted into dichloromethane (150 ml). The insolubles were filtered off. The dichloromethane solution was concentrated down to an oil. The purification was done by flash chromatography on a silica gel column (SiO2, 47 g; eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 600 ml). The material thus purified as a colorless oil, solidified on standing. Recrystallization from ethanol gave 1-[3,5-dibromo-4-[3-[4-(6-fluoro-1,2- benzisoxazol-3-yl)-1-piperidinyl]propoxy]-phenyl]ethanone as white crystals (2.93 g, 57%), m.p.=102°-103° C.

출처