Reaktion #155324

Reaktionsgleichung

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

Ausbeute 92.0%

Lösungsmittel

ethyl acetate

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGby stirring at room temperature for 16 hours
2. 2
   Sonstigethe resulting reaction mixture
3. 3
   Sonstigewas then subjected to separation
4. 4
   WaschenThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
5. 5
   TrocknenAfter being dried over anhydrous sodium sulfate
6. 6
   Einengenthe organic layer was concentrated under reduced pressure
7. 7
   SonstigeThe residue was purified
8. 8
   EinengenThe purified product was concentrated under reduced pressure

Vorschrift

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%).

Quelle