Potassium Carbonate → 1-[3-[3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-4-methoxyphenyl]-phenylmethanone

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-benzisoxazol-3-yl)-1-piperidinyl]propoxy]4-methoxyphenyl]phenylmethanone as white crystals, 3.07 g (63%), m.p.=140°-141° C.

1. temperaturewas heated
2. temperatureat reflux for 4 hours
3. customAt the end of the reaction
4. customthe solvent was evaporated
5. customthe residue was partitioned between water (150 ml) and dichloromethane (400 ml)
6. washThe dichloromethane solution was washed with water and brine (100 ml)
7. dry with materialdried over MgSO4
8. concentrationconcentrated to an oil
9. customThe purification
10. washwas done by flash chromatography over a silica gel column (SiO2, 40 g; eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 850 ml)
11. customThe material thus obtained as a colorless oil
12. customRecrystallization from ethanol (150 ml)

ORD-Eintrag

ord-5e825bbee370410cb68598bc059fc77c

Quelldatensatz

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05646161