Reacción #68091

Ecuación de reacción

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

Rendimiento 59.5%

Disolventes

acetic acid

dichloromethane

ethanol methanol

chloroform

hydrochloric acid

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred at room temperature for 1 hour
3. 3
   Otrothe organic layer was separated
4. 4
   Extracciónthe aqueous layer was extracted with chloroform
5. 5
   Lavadowashed sequentially with water and aqueous saturated sodium chloride solution
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Otrothe solvent was removed under reduced pressure
8. 8
   OtroAfter the residue thus obtained
9. 9
   Otrothe solvent was removed under reduced pressure
10. 10
    OtroTo the residue thus obtained
11. 11
    workup.ADDITIONwas added
12. 12
    Filtraciónthe resulting solid was filtered

Procedimiento

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.

Fuente