Water → 6-Chloro-4-[1-(1-quinolin-6-yl-ethyl)-piperidin-4-ylamino]-chromen-2-One

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To a solution of 6-(1-bromoethyl)-quinoline (0.44 g, 1.86 mmol) and 6-chloro-4-(piperidin-4-ylamino)-chromen-2-one (0.35 g, 1.24 mmol) in DMF (10 mL) was added K2CO3 (0.26 g, 1.86 mmol). The reaction mixture was allowed to stir at room temperature for 12 h, and was then treated with H2O (100 mL) to provide 0.52 g (96%) of a white precipitate after filtration. MS (ESI(+)Q1MS) m/z 435 (M+H)+; 1H NMR (300 MHz, DMSO) δ ppm 8.82-8.88 (m, 1H), 8.30-8.37 (m, 2H), 7.97-8.02 (m, 1H), 7.76-7.89 (m, 2H), 7.58-7.64 (m, 1H), 7.47-7.55 (m, 1H), 7.22-7.34 (m, 2H), 5.23 (s, 1H), 3.76 (dt, 1H), 3.37-3.52 (m, 1H), 2.96-3.04 (m, 1H), 2.80-2.89 (m, 1H), 2.09-2.21 (m, 2H), 1.82-1.98 (m, 2H), 1.50-1.71 (m, 2H), 1.40 (d, 3H). The pure racemic mixture was separated into enantiomers by prep HPLC chiral chromatography using a CHIRALPAK AD column: 7.5/7.5/85 MeOH/EtOH/Hexane. Enantiomers had retention times of 4.1 and 6.3 minutes. The optical rotations of the enantiomers were [α]D (90:10 CH2Cl2:MeOH, 25° C.)=+19.2 and −14.7, respectively.

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