Dimethylamine → Dimethyl carbamic acid 3-[4-(4-methoxy-phenyl)-piperazin-1-yl]-3-oxo-1-phenyl-propyl ester

Temperatur

0 °C

Ethyl benzoylacetate (2 mmol) and 4-methoxyphenylpiperazine (2 mmol) were dissolved in toluene, and refluxed for 24 hours. The resulting mixture was concentrated under a reduced pressure to obtain a crude compound, and the crude compound was dissolved in methanol, and cooled to 0° C. Then, sodium borohydride (2 mmol) was added dropwise to the resulting mixture. The 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 prepared organic phase was dried over magnesium sulfate, filtered, and then concentrated under a reduced pressure. The resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1) to obtain a compound. The prepared compound was dissolved in tetrahydrofuran (8 mL), and 1,1′-carbodiimidazole (4 mmol) was added to the resulting mixture. Then, the resulting mixture was stirred at a room temperature for 1 hour, and excessive dimethylamine 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. concentrationThe resulting mixture was concentrated under a reduced pressure
3. customto obtain a crude compound
4. concentrationconcentrated under a reduced pressure
5. additiondiluted with water
6. extractionextracted several times with ethyl acetate
7. customto obtain an organic phase
8. dry with materialThe prepared organic phase was dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under a reduced pressure
11. customThe resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1)
12. customto obtain a compound
13. stirringThen, the resulting mixture was stirred at a room temperature for 1 hour
14. customThe resulting reaction mixture
15. stirringwas stirred at a room temperature for 1 hour
16. extractionextracted several times with ethyl acetate
17. customto obtain an organic phase
18. dry with materialThe prepared organic phase was dried over magnesium sulfate
19. filtrationfiltered
20. concentrationconcentrated under a reduced pressure
21. customThe resulting pellet was purified with column chromatography (ethyl acetate)

ORD-Eintrag

ord-92f844025386451fb2a19e4064e2677d

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08541409B2