Potassium Carbonate → 4-[4-(4-Fluorobenzoyl)piperidin-1-yl]-1-(4-fluorophenyl)butan-1-one--hydrogen chloride (1/1)

A mixture of 13.9 g. (0.057 mole) of 4-(p-fluorobenzoyl)piperidine hydrochloride, 15.5 g. (0.063 mole) of 2-(p-fluorophenyl)-2-(ω-chloropropyl)-1,3-dioxolane, and 27.6 g. (0.2 mole) of potassium carbonate in 150 ml. of 1-butanol was refluxed 20 hours. The mixture was filtered, the filtrate concentrated, the oily residue dissolved in 50 ml. of an ether-methanol mixture and this solution stirred with 100 ml. of 3N HCl for one hour. The mixture was cooled, the layers separated, the aqueous layer basified and the basic mixture extracted with ether. The ethereal extracts were dried over anhydrous sodium sulfate, the mixture filtered and the filtrate treated with ethereal hydrogen chloride. The salt, which weighed 17.2 g. (74%), was recrystallized from an isopropanol-methanol mixture. The dried hydrochloride salt melted at 255°-257° C. The free base which was prepared by neutralization of a portion of the hydrochloride salt melted at 133°-135° C.

1. additionA mixture of 13.9 g
2. filtrationThe mixture was filtered
3. concentrationthe filtrate concentrated
4. dissolutionthe oily residue dissolved in 50 ml
5. temperatureThe mixture was cooled
6. customthe layers separated
7. extractionthe basic mixture extracted with ether
8. dry with materialThe ethereal extracts were dried over anhydrous sodium sulfate
9. filtrationthe mixture filtered
10. additionthe filtrate treated with ethereal hydrogen chloride
11. custom(74%), was recrystallized from an isopropanol-methanol mixture
12. customThe free base which was prepared by neutralization of a portion of the hydrochloride salt melted at 133°-135° C.

ORD record

ord-af4ae948a0a245f0af698e75d9077dd2

Source dataset

uspto-grants-1978_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04101662