120014-07-5

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• Synthesis

  A solution of 5,6-dimethoxy-indanone (19 g, 0.10 mol) in methanol (8 mL) is stirred under inert atmosphere at room temperature. Slowly add NaOH flakes (12.8 g, 0.32 mol) followed by N-benzyl-piperidine-4-carboxaldehyde (20.2 g, 0.10 mol) to the reaction mixture. The mixture was stirred at room temperature for 3 h and progress of the reaction was monitored by TLC (hexane:ethyl acetate; 1:1). Once the reaction is complete, the solid formed was filtered, washed with 5 % acetic acid and then with methanol and dried. The obtained solid (34 g) was taken into a round bottom flask and refluxed with DMF (50 mL). Gradually cooled to room temperature and stirred for 2 h, filtered the solid formed, wash with chilled methanol to afford a pale yellow crystalline solid 1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-ylindenemethyl)piperidine (32.0 g, 84 %); m.p.: 175-177 °C.
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