반응 #472814

반응 방정식

sodium hydrogen carbonate

sodium chloride

1-(2-(4-aminopiperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-one

3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde

sodium triacetoxyborohydride

→

6-(((1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-1,4-benzoxazin-3(4H)-one hydrochloride

용매

chloroform

water

dichloromethane

acetic acid

반응 조건

후처리

1. 1
   기타the organic layer was separated
2. 2
   추출the aqueous layer was extracted with chloroform
3. 3
   건조the resultant solution was dried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   기타The resultant residue was purified by silica gel column chromatography
6. 6
   workup.DISSOLUTIONmethanol=5:1, and the resultant residue was dissolved in 5 mL of 6 mol/L hydrochloric acid
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   workup.ADDITIONDiethyl ether was added to the resultant residue
9. 9
   여과the solid was filtered off

실험 절차

To a solution of 83 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-one in 15 mL of dichloromethane, 54 mg of 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde, 86 μL of acetic acid and 0.36 g of sodium triacetoxyborohydride were dividedly added while reacting at room temperature for 1.5 days. To the reaction solution, water, a saturated aqueous sodium hydrogen carbonate solution, chloroform and sodium chloride were added, the organic layer was separated, and the aqueous layer was extracted with chloroform while salting out. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=5:1, and the resultant residue was dissolved in 5 mL of 6 mol/L hydrochloric acid, and then, the solvent was distilled off under reduced pressure. Diethyl ether was added to the resultant residue, and the solid was filtered off to obtain 0.12 g of 6-(((1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-1,4-benzoxazin-3(4H)-one hydrochloride as a light yellow solid.

출처