반응 #68069

반응 방정식

N,N-dimethylformamide

ethyl 4-(3-(2-oxoquinoxalin-1(2H)-yl)propyl)piperidine-4-carboxylate

2-(2-bromoethylthio)thiophene

potassium carbonate

2-(2-bromoethylthio)thiophene

→

ethyl 4-(3-(2-oxoquinoxalin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate

수율 72.9%

용매

water

ethyl acetate

반응 조건

후처리

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   workup.STIRRINGstirred at 50-55° C. for 1 hour
3. 3
   workup.STIRRINGstirred at 60° C. for 1 hour
4. 4
   workup.ADDITIONwere added
5. 5
   기타the organic layer was separated
6. 6
   추출the aqueous layer was extracted with ethyl acetate
7. 7
   세척washed sequentially with water and aqueous saturated sodium chloride solution
8. 8
   건조dried over anhydrous magnesium sulfate
9. 9
   기타the solvent was removed under reduced pressure
10. 10
    기타The residue thus obtained
11. 11
    기타was purified by silica gel column chromatography [eluent; chloroform:methanol=20:1]

실험 절차

To 2 mL of an N,N-dimethylformamide solution containing 95 mg of ethyl 4-(3-(2-oxoquinoxalin-1(2H)-yl)propyl)piperidine-4-carboxylate, 69 mg of 2-(2-bromoethylthio)thiophene and 84 mg of potassium carbonate were added at room temperature, and stirred at 50-55° C. for 1 hour. Additional 35 mg of 2-(2-bromoethylthio)thiophene was added and stirred at 50-55° C. for 1 hour, then stirred at 60° C. for 1 hour. The mixture was cooled to the room temperature, ethyl acetate and water were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and extracts were combined, 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=20:1] to give 98 mg of ethyl 4-(3-(2-oxoquinoxalin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate as a light brown oil.

출처