Reacción #83853

Ecuación de reacción

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

K2CO3

1-[3-(3-chloropropoxy)-4-methoxy-phenyl]phenylmethanone

→

1-[3-[3-[4-(6- fluoro-1,2-benzisoxa zol-3-yl)-1-piperidinyl]propoxy]-4-methoxyphenyl]-phenylmethanone

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux for 4 hours
3. 3
   OtroAt the end of the reaction
4. 4
   Otrothe solvent was evaporated
5. 5
   Otrothe residue was partitioned between water (150 ml) and dichloromethane (400 ml)
6. 6
   LavadoThe dichloromethane solution was washed with water and brine (100 ml)
7. 7
   Secadodried over MgSO4
8. 8
   Concentraciónconcentrated to an oil
9. 9
   OtroThe purification
10. 10
    Lavadowas done by flash chromatography over a silica gel column (SiO2, 40 g; eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 850 ml)
11. 11
    OtroThe material thus obtained as a colorless oil
12. 12
    OtroRecrystallization from ethanol (150 ml)

Procedimiento

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2 benzisoxazole (2.01 g; 9.13 mmol), K2CO3 (2.0 g), and 1-[3-(3-chloropropoxy)-4-methoxy-phenyl]phenylmethanone (3.93 g; 11.3 mmol) and acetonitrile (50 ml) was heated at reflux for 4 hours. At the end of the reaction, the solvent was evaporated and the residue was partitioned between water (150 ml) and dichloromethane (400 ml). The dichloromethane solution was washed with water and brine (100 ml), dried over MgSO4, then concentrated to an oil. The purification was done by flash chromatography over a silica gel column (SiO2, 40 g; eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 850 ml). The material thus obtained as a colorless oil solidified on standing. Recrystallization from ethanol (150 ml) gave 1-[3-[3-[4-(6- fluoro-1,2-benzisoxa zol-3-yl)-1-piperidinyl]propoxy]-4-methoxyphenyl]-phenylmethanone as white crystals, 3.07 g (63%), m.p.=140°-141° C.

Fuente