반응 #83865

반응 방정식

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

K2CO3

1-[4-(3-bromopropoxy)-3-methylmercaptophenyl]ethanone

→

1-[4-[3-[4-(6-fluoro-1,2-benzoisoxazol-3-yl]-1-piperidinyl]propoxy]-3-methylmercaptophenyl]ethanone

용매

acetonitrile

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux for 4 hours
3. 3
   기타At the end of the reaction
4. 4
   농축the solvent was concentrated
5. 5
   workup.ADDITIONdiluted with dichloromethane (250 ml)
6. 6
   여과The insolubles were filtered off
7. 7
   농축The dichloromethane solution was concentrated to dryness as an oil
8. 8
   기타Purification
9. 9
   세척was effected by flash chromatography on a silica gel column (SiO2, 54 g, eluted with dichloromethane, 500 ml; 1% methanol-dichloromethane, 1.1 l)
10. 10
    기타to give a colorless oil which
11. 11
    기타Recrystallization from ethanol (100 ml)

실험 절차

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (1.88 g, 8.5 mmol), K2CO3 (1.8 g) and 1-[4-(3-bromopropoxy)-3-methylmercaptophenyl]ethanone (2.3 g, 7.6 mmol) in acetonitrile (100 ml) was heated at reflux for 4 hours. At the end of the reaction, the solvent was concentrated, then diluted with dichloromethane (250 ml). The insolubles were filtered off. The dichloromethane solution was concentrated to dryness as an oil. Purification was effected by flash chromatography on a silica gel column (SiO2, 54 g, eluted with dichloromethane, 500 ml; 1% methanol-dichloromethane, 1.1 l). The purest fractions were combined to give a colorless oil which solidified to an off-white solid (2.4 g). Recrystallization from ethanol (100 ml) yielded 1-[4-[3-[4-(6-fluoro-1,2-benzoisoxazol-3-yl]-1-piperidinyl]propoxy]-3-methylmercaptophenyl]ethanone as off-white needle crystals, 2.15 g, m.p.=150°-152° C.

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