Réaction #6194

Équation de réaction

4-(3-aminopropylthio)pyridine dihydrochloride

triethylamine

2-ethylhexanoyl chloride

→

desired compound

Rendement 92.8%

4-[3-(2-ethylhexanoylamino)propylthio]pyridine hydrochloride

Rendement 92.8%

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)

Mode opératoire

To a solution of 800 mg (3.32 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.22 ml (15.9 mmol) of triethylamine in 30 ml of methylene chloride was added 0.69 ml (3.98 mmol) of 2-ethylhexanoyl 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 1.02 g of the desired compound (free base) (quant., pale yellow oil).

Source