تفاعل #155324

معادلة التفاعل

1-bromo-3-chloropropane

DMF

8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one

sodium hydride

→

6-(3-chloropropyl)-8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one

المردود 92.0%

المذيبات

ethyl acetate

Water

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGby stirring at room temperature for 16 hours
2. 2
   أخرىthe resulting reaction mixture
3. 3
   أخرىwas then subjected to separation
4. 4
   غسيلThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
5. 5
   تجفيفAfter being dried over anhydrous sodium sulfate
6. 6
   تركيزthe organic layer was concentrated under reduced pressure
7. 7
   أخرىThe residue was purified
8. 8
   تركيزThe purified product was concentrated under reduced pressure

الإجراء التجريبي

To a DMF solution (6 ml) of 8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one (1.26 g, 3.60 mmol) was added sodium hydride (60% oil base, 189 mg, 4.33 mmol). The mixture was stirred at room temperature for 10 minutes. To the resulting mixture was added 1-bromo-3-chloropropane (1.70 g, 10.8 mmol), followed by stirring at room temperature for 16 hours. Water and ethyl acetate were added to the reaction mixture and the resulting reaction mixture was then subjected to separation. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice. After being dried over anhydrous sodium sulfate, the organic layer was concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:ethyl acetate=20:1→12:1). The purified product was concentrated under reduced pressure, giving a yellow oily substance of 6-(3-chloropropyl)-8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one (365 mg, yield: 92%).

المصدر