Реакция #155324

Уравнение реакции

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

Выход 92.0%

Растворители

ethyl acetate

Water

Условия реакции

Обработка

1. 1
   workup.STIRRINGby stirring at room temperature for 16 hours
2. 2
   Другоеthe resulting reaction mixture
3. 3
   Другоеwas then subjected to separation
4. 4
   ПромывкаThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
5. 5
   СушкаAfter being dried over anhydrous sodium sulfate
6. 6
   Концентрированиеthe organic layer was concentrated under reduced pressure
7. 7
   ДругоеThe residue was purified
8. 8
   КонцентрированиеThe purified product was concentrated under reduced pressure

Методика

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%).

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