Реакция #6195

Уравнение реакции

4-(3-aminopropylthio)pyridine dihydrochloride

triethylamine

cyclohexanoyl chloride

→

desired compound

Выход 77.0%

4-[3-(cyclohexanoylamino)propylthio]pyridine hydrochloride

Выход 77.0%

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   Температураcooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
3. 3
   ПромывкаThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
4. 4
   Другоеdried
5. 5
   workup.DISTILLATIONThe solvent was distilled off
6. 6
   ДругоеThe residue was purified by column chromatography (eluent: ethyl acetate)

Методика

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.66 ml (4.96 mmol) of cyclohexanoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 890 mg of the desired compound (free base) (77.0%, colorless prisms), mp: 93.0°-94.0° C.

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