Tetrahydro-4H-pyran-4-one → HCID 69122355, compound

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6-Chloro-5-fluoro-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride (2.0 g), Ti(iPrO)4 (4.2 mL), and tetrahydro-4H-pyran-4-one (1.4 g) were stirred together at room temperature for 1 h; dry methanol (30 mL) followed by NaBH3CN (0.8 g) were added and the mixture was stirred at room temperature for 1 h. The crude mixture was then quenched with methanol and it was purified first by SCX column chromatography followed by filtration and silica gel chromatography (methanol-NH3-dichloromethane). Conversion to the hydrochloride gave the title compound, 950 mg, MH+=336 and 338, 1H NMR (HCl salt) (DMSO-d6) 1.72 (2H, m), 1.94 (2H, m), 2.03 (2H, m), 2.81 (2H, m), 3.20 (2H, m), 3.33 (2H, m), 3.44 (1H, m), 4.01 (2H, m), 4.61 (1H, m), 7.02 (2H, m), 7.66 (1H, s), 10.52 (1H, bs) and 11.12 (1H, s).

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