Реакция #156185

Уравнение реакции

sodium hydrogencarbonate

1-methyl-6-[5-(2-pyridin-3-ylethylamino)pentyloxy]-1H-quinolin-2-one dihydrochloride

Cyclohexane carboxaldehyde

sodium

hydrogen chloride ethanol

→

title compound

(5-[cyclohexylmethyl-(2-pyridin-3-ylethyl)amino]pentyloxy}-1-methyl-1H-quinolin-2-one dihydrochloride

Растворители

ethyl acetate

1,2-dichloroethane

Triethylamine

ethanol

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   Экстракцияfollowed by extraction
3. 3
   СушкаThe organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure
4. 4
   ДругоеThe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1)
5. 5
   Другоеcondensed under reduced pressure
6. 6
   workup.STIRRINGwas stirred at room temperature
7. 7
   workup.ADDITIONwas added to the residue
8. 8
   ДругоеThe precipitated insoluble matter was separated
9. 9
   Промывкаwashed with ethyl acetate
10. 10
    Другоеdried

Методика

Triethylamine (0.15 ml) was added to a 1,2-dichloroethane solution (2.5 ml) of 1-methyl-6-[5-(2-pyridin-3-ylethylamino)pentyloxy]-1H-quinolin-2-one dihydrochloride (219 mg). The mixture was stirred at room temperature for 30 minutes. Cyclohexane carboxaldehyde (0.073 ml) and sodium triacetoxyborohydrate (159 mg) were added thereto, and the mixture was stirred at room temperature overnight. A saturated sodium hydrogencarbonate aqueous solution was added to the reaction mixture, followed by extraction using dichloromethane. The organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1). The purified product was condensed under reduced pressure. A 1N-hydrogen chloride ethanol solution (1.0 ml) was added to an ethanol solution (20 ml) of the residue, which was stirred at room temperature. The reaction mixture was condensed under reduced pressure and ethyl acetate was added to the residue. The precipitated insoluble matter was separated, washed with ethyl acetate, and dried to give the title compound (100 mg) as a pale yellow powder.

Источник