Реакция #1605851

Уравнение реакции

1-chloroethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate

butyric acid

ethyldiisopropylamine

→

1-(butyryloxy)ethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate

Растворители

diethyl ether

Условия реакции

Обработка

1. 1
   Другоеquenched with aqueous saturated NaHCO3 (40 mL)
2. 2
   ЭкстракцияThe reaction was extracted with ethyl acetate (2×50 mL)
3. 3
   Промывкаthe combined organics were washed with water (50 mL), brine (50 mL)
4. 4
   Сушкаthen dried (MgSO4)
5. 5
   ДругоеThe crude product was purified by column chromatography on silica eluting with 0.5% Et3N/ethyl acetate

Методика

1-chloroethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (2.0 g, 3.60 mmol) was stirred with butyric acid (1.0 mL, 10.81 mmol) and ethyldiisopropylamine (0.94 mL, 5.41 mmol) at 50° C. for 48 hours. The reaction was diluted with diethyl ether (20 mL) and quenched with aqueous saturated NaHCO3 (40 mL). The reaction was extracted with ethyl acetate (2×50 mL) and the combined organics were washed with water (50 mL), brine (50 mL) then dried (MgSO4). The crude product was purified by column chromatography on silica eluting with 0.5% Et3N/ethyl acetate to give 1-(butyryloxy)ethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate, Compound-90 (628 mg, 23% over 2 steps).

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