Реакция #6191

Уравнение реакции

4-(3-aminopropylthio)pyridine dihydrochloride

triethylamine

palmitoyl chloride

→

desired compound

Выход 73.8%

4-[3-(palmitoylamino)propylthio]pyridine

Выход 73.8%

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)
7. 7
   Другоеto obtain the powder which
8. 8
   Промывкаwas washed with hexane
9. 9
   Другоеdried

Методика

To a solution of 1.21 g (5.00 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.79 ml (20.0 mmol) of triethylamine in 50 ml of methylene chloride was added 1.65 ml (6.00 mmol) of palmitoyl 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 the powder which was washed with hexane and dried to obtain 1.50 g of the desired compound (73.8%, colorless powder), mp: 84.0°-85.0° C.

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