Reaktion #48499

Reaktionsgleichung

benzyl 4-aminopiperidin-1-carboxylate

triethylamine

5-bromohexanoyl chloride

→

title compound

Ausbeute 10.0%

Benzyl 4-(2-oxoazepan-1-yl)piperidin-1-carboxylate

Ausbeute 10.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
2. 2
   workup.ADDITIONthe residue was diluted with water
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe extract was washed with an aqueous 5% citric acid solution
5. 5
   Trocknena saturated saline solution, and dried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   workup.DISSOLUTIONThe residue was dissolved in DMF (40 mL)
8. 8
   Temperaturcooled at 0° C.
9. 9
   workup.ADDITIONsodium hydride (60% in oil; 0.60 g) was added
10. 10
    workup.STIRRINGthe mixture was stirred at 0° C. for one hour, at room temperature for one hour and at 80° C. for 15 hours
11. 11
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure
12. 12
    workup.ADDITIONthe residue was diluted with water
13. 13
    Extraktionextracted with ethyl acetate
14. 14
    WaschenThe extract was washed with water and saturated saline solution
15. 15
    Trocknendried over anhydrous sodium sulfate
16. 16
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
17. 17
    SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1 to 5/1)

Vorschrift

To a solution of benzyl 4-aminopiperidin-1-carboxylate (1.7 g) and triethylamine (1.1 mL) in THF (40 mL) was added dropwise 5-bromohexanoyl chloride (1.1 mL), and the mixture was stirred at 0° C. for 2 hours. The solvent was distilled off under reduced pressure and the residue was diluted with water, and extracted with ethyl acetate. The extract was washed with an aqueous 5% citric acid solution and a saturated saline solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in DMF (40 mL), and cooled at 0° C., sodium hydride (60% in oil; 0.60 g) was added thereto, and the mixture was stirred at 0° C. for one hour, at room temperature for one hour and at 80° C. for 15 hours. The solvent was distilled off under reduced pressure, the residue was diluted with water, and the solution was acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water and saturated saline solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1 to 5/1) to obtain the title compound (0.25 g, 10%) as a yellow oil.

Quelle