Reaktion #68053

Reaktionsgleichung

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

Ausbeute 82.5%

Lösungsmittel

water

Chloroform

acetic acid

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle