反応 #68069

反応方程式

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

収率 72.9%

溶媒

water

ethyl acetate

反応条件

後処理

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
   その他the organic layer was separated
6. 6
   抽出the aqueous layer was extracted with ethyl acetate
7. 7
   洗浄washed sequentially with water and aqueous saturated sodium chloride solution
8. 8
   乾燥dried over anhydrous magnesium sulfate
9. 9
   その他the solvent was removed under reduced pressure
10. 10
    その他The residue thus obtained
11. 11
    その他was purified by silica gel column chromatography [eluent; chloroform:methanol=20:1]

実験手順

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.

出典