Reaktion #72490

Reaktionsgleichung

(R)-3-hydroxy-3-phenylpropionic acid

3,4-dimethoxy phenyl piperazine

tetrahydrofuran

phenethylamine

tetrahydrofuran

EDC

HOBt

→

title compound

Phenethyl-carbamic acid-(R)-3-[4-(3,4-dimethoxy-phenyl)-piperazin-1-yl]-3-oxo-1-phenyl-propyl ester

Lösungsmittel

water

—

solvent

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONThe mixture was distilled under a reduced pressure
2. 2
   Sonstigeto remove excessive solvents
3. 3
   workup.ADDITIONwas added to the resulting mixture
4. 4
   Sonstigeto separate an organic phase
5. 5
   ExtraktionThen, the prepared organic phase was further extracted twice with 15 mL of ethyl acetate
6. 6
   TrocknenThe organic phase was dried over anhydrous magnesium sulfate (2 g)
7. 7
   Filtrationfiltered
8. 8
   Einengenthe resulting filtrate was concentrated under a reduced pressure
9. 9
   Sonstigeseparated
10. 10
    Sonstigepurified with column chromatography (hexane:ethyl acetate=1:1 to 1:10)
11. 11
    Sonstigethe resulting reaction mixture
12. 12
    workup.STIRRINGwas stirred at a room temperature for 1 hour
13. 13
    Sonstigeresulting
14. 14
    Sonstigereaction mixture
15. 15
    workup.STIRRINGwas stirred at a room temperature for additional 2 hours
16. 16
    Extraktionextracted several times with ethyl acetate
17. 17
    Sonstigeto obtain an organic phase
18. 18
    TrocknenThe prepared organic phase was dried over magnesium sulfate
19. 19
    Einengenconcentrated under a reduced pressure
20. 20
    SonstigeThe resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)

Vorschrift

(R)-3-hydroxy-3-phenylpropionic acid (1.0 g, 6.0 mmole) and 3,4-dimethoxy phenyl piperazine (1.18 g, 6.0 mmole) were dissolved in 50 mL of a solvent ‘tetrahydrofuran at a room temperature, and EDC (1.24 g, 6.0 mmole) and HOBt (0.81 g, 6 mmole) were added dropwise to the mixture. Then, the resulting mixture was stirred at 25° C. for 5 hours. The mixture was distilled under a reduced pressure to remove excessive solvents, and the solvent-free mixture was neutralized with 1 normal aqueous sodium chloride solution (20 mL), and 25 mL of ethyl acetate was added to the resulting mixture to separate an organic phase. Then, the prepared organic phase was further extracted twice with 15 mL of ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate (2 g), and filtered, and the resulting filtrate was concentrated under a reduced pressure, and separated and purified with column chromatography (hexane:ethyl acetate=1:1 to 1:10). The resulting reaction product (0.345 g, 1 mmol) was dissolved in tetrahydrofuran (15 mL), and 1,1′-carbodiimidazole (0.325 g, 2 mmol) was then added to the reaction product, and the resulting reaction mixture was stirred at a room temperature for 1 hour. Then, excessive phenethylamine was added to the reaction mixture, and resulting reaction mixture was stirred at a room temperature for additional 2 hours. 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, and concentrated under a reduced pressure. The resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate) to obtain a title compound.

Quelle