反应 #83871

反应方程式

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

K2CO3

1-[4-(3-chloropropoxy)-3-(methylamino)phenyl]ethanone

acetonitrile

→

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

收率 47.9%

溶剂

water

methanol methylene chloride

反应条件

后处理

1. 1
   温度at reflux under nitrogen for 23 hours
2. 2
   萃取the aqueous mixture was extracted with ethyl acetate
3. 3
   萃取The ethyl acetate extract
4. 4
   洗涤was washed twice with water
5. 5
   干燥dried with MgSO4
6. 6
   浓缩was concentrated
7. 7
   其他to yield 4.8 g of a damp, brown solid
8. 8
   其他Concentration of appropriate fractions afforded 2.4 g
9. 9
   其他Recrystallization from ethanol

实验过程

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.3 g, 10.3 mmol), K2CO3 (1.4 g, 10.3 mmol), 1-[4-(3-chloropropoxy)-3-(methylamino)phenyl]ethanone (2.5 g, 10.3 mmol), KI (0.10 g), and acetonitrile (100 ml) was stirred at reflux under nitrogen for 23 hours. The reaction was cooled to ambient temperature, poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was washed twice with water, dried with MgSO4 and was concentrated to yield 4.8 g of a damp, brown solid. The compound was isolated by preparative HPLC (Waters Associates prep LC/System 500, utilizing 2 silica gel columns and 4% methanol-methylene chloride as eluent). Concentration of appropriate fractions afforded 2.4 g. Recrystallization from ethanol gave 2.1 g of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-(methylamino)phenyl]ethanone as a beige solid, m.p.=151°-153° C.

来源