反应详情

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 g, 13.6 mmol), K2CO3 (2.8 g), 4-(3-bromopropoxy)-3-methoxybenzonitrile (4.0 g, 14.8 mmol) in acetonitrile (70 ml) was heated at reflux for 3 hours. At the end of the reaction, the solvent was removed on a rotary evaporator. The organic material was extracted into dichloromethane (250 ml) and the inorganics were filtered off. The dichloromethane solution was concentrated to a crude oil. The purification was done by flash chromatography over a silica gel column (SiO2, 55 g; eluted with dichloromethane, 600 ml; 1% methanol in dichloromethane, 600 ml). The material thus obtained was crystallized from a small amount of dichloromethane. Recrystallization from ethanol (25 ml) provided 3.8 g (68%) of 4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzonitrile as white crystals, m.p.=107°-108° C.

1. temperaturewas heated
2. temperatureat reflux for 3 hours
3. customAt the end of the reaction
4. customthe solvent was removed on a rotary evaporator
5. extractionThe organic material was extracted into dichloromethane (250 ml)
6. filtrationthe inorganics were filtered off
7. concentrationThe dichloromethane solution was concentrated to a crude oil
8. customThe purification
9. washwas done by flash chromatography over a silica gel column (SiO2, 55 g; eluted with dichloromethane, 600 ml; 1% methanol in dichloromethane, 600 ml)
10. customThe material thus obtained
11. customwas crystallized from a small amount of dichloromethane
12. customRecrystallization from ethanol (25 ml)