反应 #83868

反应方程式

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

K2CO3

1-[4-(3-bromopropoxy)-3-methoxyphenyl]pentanone

→

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

收率 68.7%

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
   温度the mixture was cooled
5. 5
   过滤filtered
6. 6
   浓缩The flitrate was concentrated to an oil
7. 7
   其他Purification
8. 8
   洗涤was performed by flash chromatography over a silica gel column (SiO2, 55 g; eluted with 1% methanol in dichloromethane, 600 ml; 3% methanol: 97% dichloromethane, 400 ml)
9. 9
   workup.ADDITIONThe fractions containing pure product
10. 10
    浓缩concentrated to a solid (4.3 g, 91%)
11. 11
    其他Recrystallization from ethanol (10 ml)

实验过程

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.2 g, 10 mmol), K2CO3 (3 g), 1-[4-(3-bromopropoxy)-3-methoxyphenyl]pentanone (3.7 g, 11.3 mmol) in acetonitrile (140 ml) was heated at reflux for 4 hours. At the end of the reaction, the mixture was cooled and filtered. The flitrate was concentrated to an oil. Purification was performed by flash chromatography over a silica gel column (SiO2, 55 g; eluted with 1% methanol in dichloromethane, 600 ml; 3% methanol: 97% dichloromethane, 400 ml). The fractions containing pure product were pooled and concentrated to a solid (4.3 g, 91%). Recrystallization from ethanol (10 ml) gave a powdery solid of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl )-1-piperidinyl]propoxy]-3-methoxyphenyl]-pentanone(3.22 g), m.p.=79°-80° C.

来源