Reaktion #68091

Reaktionsgleichung

1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinolin-2(1H)-one

2,3-dihydro(1,4)dioxino(2,3-c)pyridine-7-carbaldehyde

sodium hydrogen carbonate

sodium triacetoxyborohydride

→

1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxyquinolin-2(1H)-one

Ausbeute 59.5%

Lösungsmittel

acetic acid

dichloromethane

ethanol methanol

chloroform

hydrochloric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred at room temperature for 1 hour
3. 3
   Sonstigethe organic layer was separated
4. 4
   Extraktionthe aqueous layer was extracted with chloroform
5. 5
   Waschenwashed sequentially with water and aqueous saturated sodium chloride solution
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Sonstigethe solvent was removed under reduced pressure
8. 8
   SonstigeAfter the residue thus obtained
9. 9
   Sonstigethe solvent was removed under reduced pressure
10. 10
    SonstigeTo the residue thus obtained
11. 11
    workup.ADDITIONwas added
12. 12
    Filtrationthe resulting solid was filtered

Vorschrift

To 7 mL of dichloromethane solution containing 0.18 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinolin-2(1H)-one, 99 mg of 2,3-dihydro(1,4)dioxino(2,3-c)pyridine-7-carbaldehyde and 34 μL of acetic acid were added. After stirring for 5 min, 0.19 g of sodium triacetoxyborohydride was added and stirred at room temperature for 1 hour. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution and chloroform were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. After the residue thus obtained was dissolved in 6 mol/L hydrochloric acid, the solvent was removed under reduced pressure. To the residue thus obtained, a mixture of ethanol:methanol(5:1) was added and the resulting solid was filtered to give 0.16 g of 1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxyquinolin-2(1H)-one as a pale yellow solid.

Quelle