反応 #2298671

反応方程式

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

K2CO3

4-(3-bromopropoxy)-3-methoxybenzamide

→

4-[3-[4-(6-fluoro-1,2- benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxy- benzamide

収率 64.3%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux for 5 hours
3. 3
   その他At the end of the reaction the solvent
4. 4
   その他was evaporated
5. 5
   抽出The residue was extracted into dichloromethane
6. 6
   ろ過The inorganic insolubles were filtered off
7. 7
   濃縮The dichloromethane was concentrated again
8. 8
   その他The crude residue was purified by flash chromatography over a silica gel column (55 g, SiO2, eluted with 1% methanol in dichloromethane, 1 l; 2% methanol in dichloromethane, 1 l)
9. 9
   その他Recrystallization from hot ethanol (60 ml)

実験手順

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2- benzisoxazole (2.2 g, 10.0 mmoles), K2CO3 (2.0 g) and 4-(3-bromopropoxy)-3-methoxybenzamide (2.32 g, 8.0 mmoles) in acetonitrile i80 ml) was heated at reflux for 5 hours. At the end of the reaction the solvent was evaporated. The residue was extracted into dichloromethane. The inorganic insolubles were filtered off. The dichloromethane was concentrated again. The crude residue was purified by flash chromatography over a silica gel column (55 g, SiO2, eluted with 1% methanol in dichloromethane, 1 l; 2% methanol in dichloromethane, 1 l). The material thus obtained weighted 2.93 g (84%) as white crystals. Recrystallization from hot ethanol (60 ml) gave 2.2 g of 4-[3-[4-(6-fluoro-1,2- benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxy- benzamide as white crystals, m.p.=163°-164° C.

出典