반응 #472825

반응 방정식

water

ethyl 4-(3-(2-oxo-1,8-naphthyridin-1(2H)-yl)propyl)piperidine-4-carboxylate

potassium carbonate

2-((2-bromoethyl)thio)thiophene

→

ethyl 4-(3-(2-oxo-1,8-naphthyridin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate

수율 60.0%

용매

ethyl acetate

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to room temperature
2. 2
   기타the organic layer was separated
3. 3
   추출the aqueous layer was extracted with ethyl acetate
4. 4
   건조the resultant solution was dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   기타The resultant residue was purified by silica gel column chromatography

실험 절차

To a solution of 0.46 g of ethyl 4-(3-(2-oxo-1,8-naphthyridin-1(2H)-yl)propyl)piperidine-4-carboxylate in 10 mL of N,N-dimethylformamide, 0.37 g of potassium carbonate and 0.31 g of 2-((2-bromoethyl)thio)thiophene were added, and the mixture was stirred at 50 to 70° C. for 2 hours 10 minutes. The reaction mixture was cooled to room temperature, then, water and ethyl acetate were added thereto, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=50:1 to obtain 0.39 g of ethyl 4-(3-(2-oxo-1,8-naphthyridin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate as a yellow oily substance.

출처