反应 #83865

反应方程式

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

溶剂

acetonitrile

反应条件

后处理

1. 1
   温度was heated
2. 2
   温度at reflux for 4 hours
3. 3
   其他At the end of the reaction
4. 4
   浓缩the solvent was concentrated
5. 5
   workup.ADDITIONdiluted with dichloromethane (250 ml)
6. 6
   过滤The insolubles were filtered off
7. 7
   浓缩The dichloromethane solution was concentrated to dryness as an oil
8. 8
   其他Purification
9. 9
   洗涤was 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
    其他to give a colorless oil which
11. 11
    其他Recrystallization from ethanol (100 ml)

实验过程

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.

来源