Реакция #1605850

Уравнение реакции

ethyl acetate

NaH

aripiprazole

chloroethyl chloroformate

→

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

Растворители

2-methyltetrahydrofuran

2-methyltetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirring
2. 2
   workup.STIRRINGThe reaction was stirred overnight at room temperature
3. 3
   ТемператураThe reaction was cooled to 0° C.
4. 4
   Другоеquenched with aqueous saturated NaHCO3 (50 mL)
5. 5
   ЭкстракцияThe reaction was extracted with ethyl acetate (3×50 mL)
6. 6
   СушкаThe combined organics were dried (MgSO4)
7. 7
   Концентрированиеconcentrated

Методика

To a suspension of aripiprazole (2.0 g, 4.46 mmol) in 2-methyltetrahydrofuran (50 mL) was added NaH (357 mg, 8.92 mmol). The reaction was stirred overnight at room temperature then chloroethyl chloroformate (1.46 mL, 13.38 mmol) was added. Further 2-methyltetrahydrofuran (10 mL) was added to aid stirring. The reaction was stirred overnight at room temperature. The reaction was cooled to 0° C., diluted with ethyl acetate (50 mL) and quenched with aqueous saturated NaHCO3 (50 mL). The reaction was extracted with ethyl acetate (3×50 mL). The combined organics were dried (MgSO4) and concentrated to give 1-chloroethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (crude yield 2.22 g) as a 3:2 mixture of aripiprazole/product. The product was taken onto the next step without purification.

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