Реакция #68123

Уравнение реакции

N,N-dimethylformamide

ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinolin-1-yl)propyl)piperidine-4-carboxylate

potassium carbonate

N,N-dimethylformamide

(2-bromoethoxy)benzene

→

ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinolin-1-yl)propyl)-1-(2-phenoxyethyl)piperidine-4-carboxylate

Выход 90.7%

Растворители

ethyl acetate

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   workup.WAITto stand overnight
3. 3
   ДругоеThe organic layer was separated
4. 4
   Промывкаwashed with aqueous saturated sodium chloride solution
5. 5
   Сушкаdried over anhydrous magnesium sulfate
6. 6
   Другоеthe solvent was removed under reduced pressure
7. 7
   ДругоеThe residue thus obtained
8. 8
   Другоеwas purified by silica gel column chromatography [eluent; chloroform:methanol=30:1]

Методика

To 2 mL of an N,N-dimethylformamide solution containing 0.10 g of ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinolin-1-yl)propyl)piperidine-4-carboxylate, 74 mg of potassium carbonate and 1 mL of an N,N-dimethylformamide solution containing 60 mg of (2-bromoethoxy)benzene were added at room temperature. After stirred at 50° C. for 30 min, it was allowed to stand overnight. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, 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=30:1], to give 0.12 g of ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinolin-1-yl)propyl)-1-(2-phenoxyethyl)piperidine-4-carboxylate as a yellow oil.

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