Reacción #6198

Ecuación de reacción

4-(3-aminopropylthio) pyridine dihydrochloride

trietylamine

1-naphthoyl chloride

→

desired compound

Rendimiento 74.8%

4-[3-(1-naphthoylamino)propylthio]pyridine hydrochloride

Rendimiento 74.8%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
3. 3
   LavadoThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
4. 4
   Otrodried
5. 5
   workup.DISTILLATIONThe solvent was distilled off
6. 6
   OtroThe residue was purified by column chromatography (eluent: methanol/ ethyl acetate=1:10)
7. 7
   Otroto obtain the powder which
8. 8
   Lavadowas washed with ether
9. 9
   Otrodried

Procedimiento

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio) pyridine dihydrochloride and 2.78 ml (19.9 mmol) of trietylamine in 40 ml of methylene chloride was added 0.75 ml (4.98 mmol) of 1-naphthoyl 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: methanol/ ethyl acetate=1:10) to obtain the powder which was washed with ether and dried to obtain 1.00 g of the desired compound (free base) (74.8%, yellow powder), mp: 113.0°-114.0° C.

Fuente