Reaktion #68086

Reaktionsgleichung

hydrochloric acid

ethyl 1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate

(2,3-dihydro-1,4-benzodioxin-6-yl)acetaldehyde

sodium triacetoxyborohydride

→

ethyl 4-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate

Ausbeute 68.2%

Lösungsmittel

water

chloroform

acetic acid

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirred at room temperature for 1 hour
3. 3
   SonstigeThe organic layer was separated
4. 4
   workup.ADDITIONby adding 5 mol/L aqueous sodium hydroxide solution to the aqueous layer
5. 5
   Extraktionextracted with chloroform
6. 6
   Waschenwashed with aqueous saturated sodium chloride solution
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Sonstigethe solvent was removed under reduced pressure
9. 9
   SonstigeThe residue thus obtained
10. 10
    Sonstigewas purified by silica gel column chromatography [eluent; chloroform:methanol=50:1]

Vorschrift

To 2.4 mL of dichloromethane solution containing 89 mg of ethyl 1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate and 94 mg of (2,3-dihydro-1,4-benzodioxin-6-yl)acetaldehyde, 24 μL of acetic acid was added and stirred at room temperature for 30 min. To the reaction mixture, 76 mg of sodium triacetoxyborohydride was added, and stirred at room temperature for 1 hour. To the reaction mixture, chloroform and water were added, and adjusted to pH 1 with 6 mol/L hydrochloric acid. The organic layer was separated, and adjusted to pH 13 by adding 5 mol/L aqueous sodium hydroxide solution to the aqueous layer, thereafter 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=50:1], to give 87 mg of ethyl 4-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate as a colorless oil.

Quelle