Реакция #1605852

Уравнение реакции

aripiprazole

NaH

Chloro(phenyl)methyl carbonochloridate

→

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

Растворители

2-methyltetrahydrofuran

ethyl acetate

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was heated
2. 2
   Температураto reflux for 1.5 hours
3. 3
   ТемператураThe reaction was cooled to 0° C.
4. 4
   Другоеquenched with aqueous saturated NaHCO3 (20 mL) solution
5. 5
   ЭкстракцияThe reaction was extracted with ethyl acetate (3×20 mL)
6. 6
   Промывкаthe combined organics washed with brine (50 mL)
7. 7
   Сушкаdried (MgSO4)
8. 8
   Концентрированиеconcentrated

Методика

To a suspension of aripiprazole (1 g, 2.23 mmol) in 2-methyltetrahydrofuran (20 mL) was added NaH (178 mg, 4.46 mmol). The reaction was heated to reflux for 1.5 hours then cooled to room temperature. Chloro(phenyl)methyl carbonochloridate (1.37 g, 6.69 mmol) was then added and the reaction stirred overnight at room temperature. The reaction was cooled to 0° C., diluted with ethyl acetate (20 mL) and quenched with aqueous saturated NaHCO3 (20 mL) solution. The reaction was extracted with ethyl acetate (3×20 mL) and the combined organics washed with brine (50 mL), then dried (MgSO4) and concentrated to give chloro(phenyl)methyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (crude yield 2.10 g) as a 1:3 mixture of product/aripiprazole. The product was taken onto the next step crude.

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