Reaktion #68078

Reaktionsgleichung

N,N-dimethylformamide

ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

potassium carbonate

N,N-dimethylformamide

2-(2-bromoethylthio)thiophene

→

ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate

Lösungsmittel

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To 1.25 mL of an N,N-dimethylformamide solution containing 70 mg of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 57 mg of potassium carbonate and 0.25 mL of N,N-dimethylformamide containing 47 mg of 2-(2-bromoethylthio)thiophene were added at room temperature, and stirred at 60° C. for 3 hours. To the reaction mixture, ethyl acetate and water were added. The organic layer was separated, washed sequentially with water and 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 91 mg of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate as a yellow oil.

Quelle