Carbon Tetrachloride → HCID 69642317, compound

To a suspension of ethyl 4-[methyl[(phenylamino)thioxomethyl]amino]-1-piperidinecarboxylate (4.02 g, 12.5 mmol) in carbon tetrachloride (25 mL) was added dropwise a solution of bromine (2.00 g, 12.5 mmol) in carbon tetrachloride (10 mL), the mixture was stirred at room temperature for 30 minutes, and heated to reflex for 1 hours. The insolubles were filtered, and washed with hexane. This was dissolved in 48% hydrobromic acid (40 mL), and the solution was heated to reflux for 2 hours. The reaction mixture was ice-cooled, neutralized with 25% aqueous ammonia, and extracted with ethyl acetate two times. The combined organic layers were washed with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. To the residue was added diisopropyl ether, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol, a 10% hydrogen chloride-methanol solution (11 mL), and the mixture was concentrated under reduced pressure. The residue was recrystallized from methanol-diisopropyl ether to obtain 2.53 g of the title compound.

1. temperatureheated
2. waitto reflex for 1 hours
3. filtrationThe insolubles were filtered
4. washwashed with hexane
5. dissolutionThis was dissolved in 48% hydrobromic acid (40 mL)
6. temperaturethe solution was heated
7. temperatureto reflux for 2 hours
8. temperaturecooled
9. extractionextracted with ethyl acetate two times
10. washThe combined organic layers were washed with water and saturated brine
11. dry with materialdried over magnesium sulfate
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. additionTo the residue was added diisopropyl ether
15. filtrationthe insolubles were filtered
16. concentrationthe filtrate was concentrated under reduced pressure
17. dissolutionThe residue was dissolved in methanol
18. concentrationa 10% hydrogen chloride-methanol solution (11 mL), and the mixture was concentrated under reduced pressure
19. customThe residue was recrystallized from methanol-diisopropyl ether

ORD record

ord-a286a3fa80784051898279a55f1e74ba

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07008940B1