Реакция #68091

Уравнение реакции

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

Выход 59.5%

Растворители

acetic acid

dichloromethane

ethanol methanol

chloroform

hydrochloric acid

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred at room temperature for 1 hour
3. 3
   Другоеthe organic layer was separated
4. 4
   Экстракцияthe aqueous layer was extracted with chloroform
5. 5
   Промывкаwashed sequentially with water and aqueous saturated sodium chloride solution
6. 6
   Сушкаdried over anhydrous magnesium sulfate
7. 7
   Другоеthe solvent was removed under reduced pressure
8. 8
   ДругоеAfter the residue thus obtained
9. 9
   Другоеthe solvent was removed under reduced pressure
10. 10
    ДругоеTo the residue thus obtained
11. 11
    workup.ADDITIONwas added
12. 12
    Фильтрацияthe resulting solid was filtered

Методика

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.

Источник