반응 #83884

반응 방정식

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

용매

ethanol

ethanol

acetonitrile

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux for 3 hours
3. 3
   기타At the end of the reaction
4. 4
   온도the reaction was cooled
5. 5
   여과filtered
6. 6
   세척the solids washed with dichloromethane (100 ml)
7. 7
   기타The organic solvent was removed on a rotary evaporator
8. 8
   기타to leave a crude oil (18 g)
9. 9
   기타Purification
10. 10
    기타The product thus purified
11. 11
    기타Analytically pure sample was prepared

실험 절차

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (9.25 g, 42 mmol), K2CO3 (8 g, 58 mmol) and 3-(3-acetamidophenoxy)propyl bromide (11.4 g, 42 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 of 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.

출처