Sodium hydride → 2-[1-(2-Butyl4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-yl)-indan-5-yl]-benzonitrile

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Sodium hydride (53 mg, 2.3 mmol) was added to 2-butyl-1,3-diaza-spiro[4.4]non-1-en-4-one (458 mg, 2.36 mmol) in anhydrous 1,4-dioxane (3 mL). After 0.25 hour, a solution of 2-(1-chloro-indan-5-yl)-benzonitrile (300 mg, 1.18 mmol)in dioxane (1.0 mL) was added. The reaction mixture was heated at 110° C. for 20 hours, cooled to room temperature and concentrated in vacuo. The crude residue was chromatographed on SiO2 -gel using 50% ethyl acetate/hexanes to give 150 mg of a colorless oil. 1H NMR (250 MHz, CDCl3): d 7.80 (d, 1 H), 7.65 (q, 1 H), 7.48 (m, 4 H), 7.10 (d, 1 H), 5.75 (m, 1 H), 3.42 (m), 3.15 (m), 2.85 (m), 2.55 (m), 2.40-1.60 (m), 1.40 (m), 0.88 (t, 3 H).

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