반응 #68227

반응 방정식

sodium cyanoborohydride

methanol

1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide

2-naphthoaldehyde

→

7-methoxy-N-methyl-1-(2-(4-((naphthalen-2-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxamide

수율 119.6%

용매

acetic acid

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred at the same temperature for 75 min
3. 3
   기타After the solvent was removed under reduced pressure, chloroform and aqueous saturated sodium hydrogen carbonate solution
4. 4
   workup.ADDITIONwere added
5. 5
   기타the organic layer was separated
6. 6
   추출the aqueous layer was extracted with chloroform
7. 7
   세척washed with aqueous saturated sodium chloride solution
8. 8
   건조dried over anhydrous magnesium sulfate
9. 9
   기타the solvent was removed under reduced pressure
10. 10
    기타The residue thus obtained
11. 11
    기타was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; chloroform:methanol=30:1]

실험 절차

To 4 mL of a methanol solution containing 0.14 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide, 55 mg of 2-naphthoaldehyde and 40 μL of acetic acid were added, and stirred at room temperature for 80 min. To the reaction mixture, 52 mg of sodium cyanoborohydride was added, and stirred at the same temperature for 75 min. After the solvent was removed under reduced pressure, chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; chloroform:methanol=30:1], to give 0.21 g of 7-methoxy-N-methyl-1-(2-(4-((naphthalen-2-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxamide as a yellow foam.

출처