반응 #68091

반응 방정식

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

수율 59.5%

용매

acetic acid

dichloromethane

ethanol methanol

chloroform

hydrochloric acid

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred at room temperature for 1 hour
3. 3
   기타the organic layer was separated
4. 4
   추출the aqueous layer was extracted with chloroform
5. 5
   세척washed sequentially with water and aqueous saturated sodium chloride solution
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   기타the solvent was removed under reduced pressure
8. 8
   기타After the residue thus obtained
9. 9
   기타the solvent was removed under reduced pressure
10. 10
    기타To the residue thus obtained
11. 11
    workup.ADDITIONwas added
12. 12
    여과the resulting solid was filtered

실험 절차

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.

출처