Reaktion #6198

Reaktionsgleichung

4-(3-aminopropylthio) pyridine dihydrochloride

trietylamine

1-naphthoyl chloride

→

desired compound

Ausbeute 74.8%

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

Ausbeute 74.8%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle