تفاعل #1605846

معادلة التفاعل

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

cesium acetate

→

acetoxymethyl 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 0-10% 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 0.5% Et3N/ethyl acetate

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 cesium acetate (639 mg, 3.33 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 0-10% tetrahydrofuran/dichloromethane with 1% Et3N to give the product which required further purification. The product was purified by column chromatography on silica eluting with 0.5% Et3N/ethyl acetate to give acetoxymethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate, Compound-87 (243 mg, 19% over 2 steps).

المصدر