Réaction #155324

Équation de réaction

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

Rendement 92.0%

Solvants

ethyl acetate

Water

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGby stirring at room temperature for 16 hours
2. 2
   Autrethe resulting reaction mixture
3. 3
   Autrewas then subjected to separation
4. 4
   LavageThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
5. 5
   SéchageAfter being dried over anhydrous sodium sulfate
6. 6
   Concentrationthe organic layer was concentrated under reduced pressure
7. 7
   AutreThe residue was purified
8. 8
   ConcentrationThe purified product was concentrated under reduced pressure

Mode opératoire

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%).

Source