反应 #83853

反应方程式

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

K2CO3

1-[3-(3-chloropropoxy)-4-methoxy-phenyl]phenylmethanone

→

1-[3-[3-[4-(6- fluoro-1,2-benzisoxa zol-3-yl)-1-piperidinyl]propoxy]-4-methoxyphenyl]-phenylmethanone

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
   其他the solvent was evaporated
5. 5
   其他the residue was partitioned between water (150 ml) and dichloromethane (400 ml)
6. 6
   洗涤The dichloromethane solution was washed with water and brine (100 ml)
7. 7
   干燥dried over MgSO4
8. 8
   浓缩concentrated to an oil
9. 9
   其他The purification
10. 10
    洗涤was done by flash chromatography over a silica gel column (SiO2, 40 g; eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 850 ml)
11. 11
    其他The material thus obtained as a colorless oil
12. 12
    其他Recrystallization from ethanol (150 ml)

实验过程

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2 benzisoxazole (2.01 g; 9.13 mmol), K2CO3 (2.0 g), and 1-[3-(3-chloropropoxy)-4-methoxy-phenyl]phenylmethanone (3.93 g; 11.3 mmol) and acetonitrile (50 ml) was heated at reflux for 4 hours. At the end of the reaction, the solvent was evaporated and the residue was partitioned between water (150 ml) and dichloromethane (400 ml). The dichloromethane solution was washed with water and brine (100 ml), dried over MgSO4, then concentrated to an oil. The purification was done by flash chromatography over a silica gel column (SiO2, 40 g; eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 850 ml). The material thus obtained as a colorless oil solidified on standing. Recrystallization from ethanol (150 ml) gave 1-[3-[3-[4-(6- fluoro-1,2-benzisoxa zol-3-yl)-1-piperidinyl]propoxy]-4-methoxyphenyl]-phenylmethanone as white crystals, 3.07 g (63%), m.p.=140°-141° C.

来源