Methyl Isobutyl Ketone → 4-[4-[2-(Indan-2-yl)ethyl]piperazin-1-yl]-1H-indole

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Reaction Steps

A mixture of 4-(piperazin-1-yl)-1H-indole (1.5 g), 2-(2-iodoethyl)indane (2.0 g), K2C(3, methyl isobutyl ketone (150 ml), and N-methylpyrrolidone (10 ml ) was boiled under reflux for 3 h. The mixture was allowed to cool to room temperature, filtered, and concentrated in vacuo. The residue was purified on silica gel eluted with ethyl acetate-heptane (1:2) to give a crystalline compound, which was recrystallized (ethyl acetate) to give the title compound (1.2 g, 47%). Mp 146-147° C. 1H NMR (CDCl3) δ 1.70-1.85 (m, 2H), 2.40-2.70 (m, 5H), 2.75 (broad s, 4H), 3.00-3.15 (m, 2H), 3.30 (broad s, 4H), 6.55 (s, 1H), 6.60 (d, 1H), 7.00-7.30 (m, 711), 8.20 (broad s, 1H). MS m/z (%): 346 (MH+, 34%), 159 (88%), 145 (100%).

Provenance & Evidence