Réaction #6191

Équation de réaction

4-(3-aminopropylthio)pyridine dihydrochloride

triethylamine

palmitoyl chloride

→

desired compound

Rendement 73.8%

4-[3-(palmitoylamino)propylthio]pyridine

Rendement 73.8%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
3. 3
   LavageThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
4. 4
   Autredried
5. 5
   workup.DISTILLATIONThe solvent was distilled off
6. 6
   AutreThe residue was purified by column chromatography (eluent: ethyl acetate)
7. 7
   Autreto obtain the powder which
8. 8
   Lavagewas washed with hexane
9. 9
   Autredried

Mode opératoire

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.

Source