반응 #68053

반응 방정식

sodium hydrogen carbonate

(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde

N-(piperidin-4-yl)-2,3-dihydro-1,4-benzodioxin-6-sulfonamide

sodium triacetoxyborohydride

→

N-(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)-2,3-dihydro-1,4-benzodioxin-6-sulfonamide

수율 82.5%

용매

water

Chloroform

acetic acid

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred at the same temperature for 2 hours
3. 3
   기타The organic layer was separated
4. 4
   추출the aqueous layer was extracted with chloroform
5. 5
   세척washed with aqueous saturated sodium chloride solution
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   기타the solvent was removed under reduced pressure
8. 8
   기타The residue thus obtained
9. 9
   기타was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

실험 절차

To 2 mL of dichloromethane solution containing 30 mg of (7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde, 39 mg of N-(piperidin-4-yl)-2,3-dihydro-1,4-benzodioxin-6-sulfonamide and 7.4 μl of acetic acid were added and stirred at room temperature for 2 hours. To the reaction mixture, 41 mg of sodium triacetoxyborohydride was added and stirred at the same temperature for 2 hours. Chloroform and water were added, and adjusted to pH 7.8 with aqueous saturated sodium hydrogen carbonate solution. 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 [eluent; chloroform:methanol=10:1] to give 55 mg of N-(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)-2,3-dihydro-1,4-benzodioxin-6-sulfonamide as a light brown foam.

출처