Ammonium Chloride → HCID 23149876, compound

Temperature

0 °C

A 5-chlorothienyl magnesium bromide-tetrahydrofuran solution (Aldrich Co., 0.5 M, 22 ml) was cooled to 0° C., and 1-(tert-butoxycarbonyl)-4-piperidone (Aldrich Co. (hereafter the same), 2.0 g) was dissolved in tetrahydrofuran (10 ml) and added thereto. The mixture was heated under reflux for 8 hr. After completion of the reaction, the mixture was cooled to 0° C. A saturated aqueous ammonium chloride solution was added, and a solid was filtered off. The filtrate was extracted with diethyl ether. The organic layer was dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent:hexane-ethyl acetate (5:1)). The intermediate was dissolved in ethyl acetate, and a 4N hydrochloric acid-ethyl acetate solution (3 ml) was added. The mixture was stirred at room temperature for 3 hr. After completion of the reaction, the solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give 4-(5-chloro-2-thienyl)-1,2,3,6-tetrahydropyridine hydrochloride (637 mg, yield 23%).

1. additionadded
2. temperatureThe mixture was heated
3. temperatureunder reflux for 8 hr
4. customAfter completion of the reaction
5. filtrationa solid was filtered off
6. extractionThe filtrate was extracted with diethyl ether
7. customThe organic layer was dried
8. customthe solvent was evaporated under reduced pressure
9. customThe obtained residue was purified by silica gel column chromatography (elution solvent:hexane-ethyl acetate (5:1))
10. dissolutionThe intermediate was dissolved in ethyl acetate
11. additiona 4N hydrochloric acid-ethyl acetate solution (3 ml) was added
12. customAfter completion of the reaction
13. customthe solvent was evaporated under reduced pressure
14. filtrationThe precipitated solid was collected by filtration

ORD record

ord-5f73754b7fd04035be020cd7e20a08f8

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994196B2