تفاعل #1605847

معادلة التفاعل

cesium carbonate

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

butyric acid

→

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

المذيبات

ethyl acetate

dimethyl formamide

ظروف التفاعل

المعالجة

1. 1
   أخرىquenched with water/brine (1:1, 50 mL)
2. 2
   استخلاصThe reaction was extracted with ethyl acetate (3×50 mL)
3. 3
   غسيلThe combined organics were washed with water (50 mL)
4. 4
   تجفيفbrine (50 mL) and dried (MgSO4)
5. 5
   تركيزconcentrated
6. 6
   أخرىThe crude product was purified by column chromatography on silica eluting with 010% tetrahydrofuran/dichloromethane with 1% Et3N
7. 7
   أخرىto give the product which
8. 8
   أخرىpurification
9. 9
   أخرىThe product was purified by column chromatography on silica eluting with 0

الإجراء التجريبي

To a solution of chloromethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (1.20 g, 2.22 mmol) in dimethyl formamide (20 mL) was added butyric acid (0.30 mL, 3.33 mmol) followed by cesium carbonate (542 mg, 1.67 mmol). The reaction was then stirred at ambient temperature overnight. The reaction was diluted with ethyl acetate (50 mL) and quenched with water/brine (1:1, 50 mL). The reaction was extracted with ethyl acetate (3×50 mL). The combined organics were washed with water (50 mL) then brine (50 mL) and dried (MgSO4) and concentrated. The crude product was purified by column chromatography on silica eluting with 010% tetrahydrofuran/dichloromethane with 1% Et3N to give the product which required further purification. The product was purified by column chromatography on silica eluting with 0.51.5% Et3N/ethyl acetate to give butyryloxymethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate, Compound-88 (348 mg, 26% over 2 steps).

المصدر