Реакция #155351

Уравнение реакции

Sodium triacetoxyborohydride

1-(2-Pyridyl)piperazine

5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carbaldehyde

→

5-fluoro-3-(4-methoxyphenyl)-8-propoxy-2-(4-pyridin-2-yl-piperazin-1-ylmethyl)-1H-quinolin-4-one

Выход 35.4%

Растворители

Dichloromethane

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred at room temperature for 4 hours
2. 2
   Промывкаwashed with water
3. 3
   Сушкаthe mixture was dried over sodium sulfate
4. 4
   ДругоеThereafter, the solvent was removed under reduced pressure
5. 5
   ДругоеThe residue was then purified
6. 6
   ДругоеThe solvent was removed under reduced pressure
7. 7
   Другоеthe residue was recrystallized from ethyl acetate-n-hexane

Методика

1-(2-Pyridyl)piperazine (551 mg, 3.38 mmol) was added to a 1,2-dichloromethane solution (20 ml) of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carbaldehyde (800 mg, 2.25 mmol) and stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (670 mg, 3.16 mmol) was added to the resulting mixture and stirred at room temperature for 4 hours. Dichloromethane was added to the resulting reaction mixture, washed with water, and then the mixture was dried over sodium sulfate. Thereafter, the solvent was removed under reduced pressure. The residue was then purified using NH silica gel column chromatography (dichloromethane:ethyl acetate=1:1). The solvent was removed under reduced pressure and the residue was recrystallized from ethyl acetate-n-hexane, giving a white powder of 5-fluoro-3-(4-methoxyphenyl)-8-propoxy-2-(4-pyridin-2-yl-piperazin-1-ylmethyl)-1H-quinolin-4-one (400 mg, yield: 35%).

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