反应 #83864

反应方程式

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

1-[4-(3-chloropropoxy)-3-methoxyphenyl]-2,2,2-trifluoroethanone

K2CO3

acetonitrile

→

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

收率 56.0%

溶剂

water

反应条件

后处理

1. 1
   温度refluxed for 16 hours
2. 2
   温度After cooling
3. 3
   萃取the aqueous mixture extracted with ethyl acetate
4. 4
   洗涤The extract was washed (H2O)
5. 5
   干燥dried (MgSO4)
6. 6
   浓缩the solvent was concentrated to an oil, which upon evacuation at high vacuum
7. 7
   其他afforded 3.2 g of a waxy solid
8. 8
   其他The solid was chromatographed on a Waters preparative LC (silica columns, eluting with 3% methanol-dichloromethane)

实验过程

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (1.5 g, 6.7 mmol), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]-2,2,2-trifluoroethanone (2.0 g, 6.7 mmol), K2CO3 (0.88 g), KI (0.1 g) and acetonitrile (50 ml) was stirred and refluxed for 16 hours. After cooling, the reaction was poured into water and the aqueous mixture extracted with ethyl acetate. The extract was washed (H2O), dried (MgSO4), and the solvent was concentrated to an oil, which upon evacuation at high vacuum afforded 3.2 g of a waxy solid. The solid was chromatographed on a Waters preparative LC (silica columns, eluting with 3% methanol-dichloromethane). Concentration of the appropriate fractions gave 1.8 g (56%) of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-propoxy]-3-methoxyphenyl]-2,2,2-trifluoro-ethanone solid, m.p.=94°-96° C.

来源