Ethyl benzoylacetate → Carbamic acid 3-[4-(4-fluoro-phenyl)-piperazin-1-yl]-3-oxo-1-phenyl-propyl ester

Temperatur

0 °C

Ethyl benzoylacetate (2.887 mmol) and 4-fluorophenylpiperazine (2.887 mmol) were dissolved in toluene, and refluxed for 24 hours. The resulting reaction mixture was concentrated under a reduced pressure, and dissolved in methanol, and cooled to 0° C., and sodium borohydride (2.887 mmol) was then added dropwise to the resulting mixture. The resulting mixture was stirred at a room temperature for 2 hours, concentrated under a reduced pressure, diluted with water, and then extracted several times with ethyl acetate to obtain an organic phase. The resulting organic phase was dried over magnesium sulfate, filtered, and then concentrated under a reduced pressure. The resulting mixture was purified with column chromatography (hexane:ethyl acetate=1:1) to obtain a compound. The prepared compound was dissolved in tetrahydrofuran (10 mL), and 1,1′-carbodiimidazole (5 mmol) was added to the resulting mixture. Then, the resulting mixture was stirred at a room temperature for 1 hour, and excessive ammonium hydroxide was added to the reaction mixture. The resulting reaction mixture was stirred at a room temperature for 1 hour. The reaction mixture was diluted with water, and extracted several times with ethyl acetate to obtain an organic phase. The prepared organic phase was dried over magnesium sulfate, filtered, and then concentrated under a reduced pressure. The resulting pellet was purified with column chromatography (ethyl acetate) to obtain a title compound.

1. temperaturerefluxed for 24 hours
2. customThe resulting reaction mixture
3. concentrationwas concentrated under a reduced pressure
4. dissolutiondissolved in methanol
5. concentrationconcentrated under a reduced pressure
6. additiondiluted with water
7. extractionextracted several times with ethyl acetate
8. customto obtain an organic phase
9. dry with materialThe resulting organic phase was dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated under a reduced pressure
12. customThe resulting mixture was purified with column chromatography (hexane:ethyl acetate=1:1)
13. customto obtain a compound
14. stirringThen, the resulting mixture was stirred at a room temperature for 1 hour
15. customThe resulting reaction mixture
16. stirringwas stirred at a room temperature for 1 hour
17. extractionextracted several times with ethyl acetate
18. customto obtain an organic phase
19. dry with materialThe prepared organic phase was dried over magnesium sulfate
20. filtrationfiltered
21. concentrationconcentrated under a reduced pressure
22. customThe resulting pellet was purified with column chromatography (ethyl acetate)

ORD-Eintrag

ord-d372ebc6ef204fdbae1a51f5b0d0894d

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08901116B2