تفاعل #6198

معادلة التفاعل

4-(3-aminopropylthio) pyridine dihydrochloride

trietylamine

1-naphthoyl chloride

→

desired compound

المردود 74.8%

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

المردود 74.8%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر