Reaktion #68043

Reaktionsgleichung

N,N-dimethylformamide

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

potassium carbonate

2-(2-bromoethylthio)thiophene

→

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

Ausbeute 68.1%

Lösungsmittel

ethyl acetate

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Sonstigethe organic layer was separated
3. 3
   Extraktionthe aqueous layer was extracted with ethyl acetate
4. 4
   Waschenwashed with aqueous saturated sodium chloride solution
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Sonstigethe solvent was removed under reduced pressure
7. 7
   SonstigeThe residue thus obtained
8. 8
   Sonstigewas purified by silica gel column chromatography [eluent; chloroform:methanol=100:1]

Vorschrift

To 4 mL of an N,N-dimethylformamide solution containing 0.29 g of ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 0.25 g of potassium carbonate and 0.20 g of 2-(2-bromoethylthio)thiophene were added and stirred at 60-70° C. for 2 hours. Water and ethyl acetate were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. 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=100:1] to give 0.27 g of ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate as a pale yellow oil.

Quelle