Potassium Carbonate → HCID 131718068, compound

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (4.53 g, 20.5 mmol), K2CO3 (4.5 g), 1-[3-(3-chloropropoxy)phenyl]ethanone (6.4 g, 29 mmol) in acetonitrile (60 ml) was heated at reflux for 5 hours. At the end of the reaction, the solvent was removed and the residue was extracted into dichloromethane (300 ml). The inorganic insolubles were filtered off. The dichloromethane solution was concentrated to a small volume (10 ml) and purified on a flash chromatographic column (SiO2, 75 g, eluted with dichloromethane, 900 ml; and 2% methanol in dichloromethane, 800 ml). The fractions containing the pure product were combined and concentrated to an oil (2.87 g, 35%). The oil was dissolved into ethanol and treated with a solution of fumaric acid (841 mg). Recrystallization (twice) from ethanol afforded 2.53 g of 1-[3-[3-[4-(6-fluoro-1,2-benzisoxazo]-3-yl)-1-piperidinyl]propoxy]phenyl]ethanone fumarate as white crystals, m.p.=172°-174° C.

1. temperaturewas heated
2. temperatureat reflux for 5 hours
3. customAt the end of the reaction
4. customthe solvent was removed
5. extractionthe residue was extracted into dichloromethane (300 ml)
6. filtrationThe inorganic insolubles were filtered off
7. concentrationThe dichloromethane solution was concentrated to a small volume (10 ml)
8. custompurified on a flash chromatographic column (SiO2, 75 g, eluted with dichloromethane, 900 ml; and 2% methanol in dichloromethane, 800 ml)
9. additionThe fractions containing the pure product
10. concentrationconcentrated to an oil (2.87 g, 35%)
11. dissolutionThe oil was dissolved into ethanol
12. additiontreated with a solution of fumaric acid (841 mg)
13. customRecrystallization (twice) from ethanol

ORD record

ord-bf0c8c37f5c64237b4fe9908f4557edd

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05843949