Reaktion #68133

Reaktionsgleichung

potassium hydroxide

1,4-dioxane

4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)cyclohexanecarbonitrile

potassium hydroxide

ethanol

→

4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)cyclohexanecarboxamide

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   Temperaturrefluxed
3. 3
   Temperaturwith heating for 4 hours
4. 4
   Temperaturrefluxed
5. 5
   Temperaturwith heating for 4 hours
6. 6
   Temperaturrefluxed
7. 7
   Temperaturwith heating for 3 hours
8. 8
   Sonstigethe solvent was removed under reduced pressure
9. 9
   workup.ADDITIONwas added
10. 10
    SonstigeThe organic layer was separated
11. 11
    Waschenwashed with aqueous saturated sodium chloride solution
12. 12
    Trocknendried over anhydrous magnesium sulfate
13. 13
    Sonstigethe solvent was removed under reduced pressure
14. 14
    SonstigeTo the residue thus obtained
15. 15
    Filtrationthe resulting solid was filtered

Vorschrift

To 1.5 mL of a 1,4-dioxane solution containing 90 mg of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)cyclohexanecarbonitrile, 1 mL of 20% aqueous potassium hydroxide solution and 1 mL of ethanol were added at room temperature and refluxed with heating for 4 hours. Further, 1 mL of 20% aqueous potassium hydroxide solution was added and refluxed with heating for 4 hours, 2 mL of the solution was added and for 9.5 hours, 1 mL of the solution was added and for 1 hour, 1 mL of the solution was added and for 8 hours, further 1 mL of the solution was added and refluxed with heating for 3 hours. The reaction mixture was cooled to the room temperature, and the solvent was removed under reduced pressure. The residue was adjusted to pH 11 with 2.0 mol/L hydrochloric acid and ethyl acetate was added. The organic layer was separated, and washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue thus obtained, diethyl ether was added, and the resulting solid was filtered to give 53 mg of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)cyclohexanecarboxamide as a white solid.

Quelle