反应 #2271697

反应方程式

fumaric acid

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

K2CO3

3-(3-acetamidophenoxy)propyl bromide

→

N-[3-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]phenyl]acetamide hemifumarate

溶剂

ethanol

ethanol

acetonitrile

反应条件

后处理

1. 1
   温度was heated
2. 2
   温度at reflux for 3 hours
3. 3
   其他At the end of the reaction
4. 4
   温度the reaction was cooled
5. 5
   过滤filtered
6. 6
   洗涤the solids washed with dichloromethane (100 ml)
7. 7
   其他The organic solvent was removed on a rotary evaporator
8. 8
   其他to leave a crude oil (18 g)
9. 9
   其他Purification
10. 10
    其他The product thus purified
11. 11
    其他Analytically pure sample was prepared

实验过程

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (9.25 g, mmol), K2CO3 (8 g, 58 mmol) and 3-(3-acetamidophenoxy)propyl bromide (11.4 g, mmol) in acetonitrile (350 ml) was heated at reflux for 3 hours. At the end of the reaction, the reaction was cooled, filtered and the solids washed with dichloromethane (100 ml). The organic solvent was removed on a rotary evaporator to leave a crude oil (18 g). Purification was by flash chromatography on a silica gel column. The product thus purified was an oil, 12.2 g, 70%. Analytically pure sample was prepared by dissolving 3 g or free base in ethanol and treating with fumaric acid solution in ethanol (850 mg: 5 ml). The N-[3-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]phenyl]acetamide hemifumarate crystals obtained weighed 2.73 g, m.p.=184°-186° C. ANALYSIS: Calculated for C23H26FN3O20.5C4H4O4: 63.95%C 6.01%H 8.94%N Found: 63.47%C 5.94%,H 8.78%N

来源