Triethylamine → 7-{4-[4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-butoxy}-4-methyl-3,4-dihydro-1H-[1,8]naphthyridin-2-one

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The crude 4-(5-methyl-7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde in 1,2-dichloroethane (50 mL) is treated with 1-(2,3-dichlorophenyl)piperazine monohydrochloride (1.104 g, 4.13 mmol), followed by triethylamine (0.80 mL, 5.69 mmol) and sodium triacetoxyborohydride (0.911 g, 4.30 mmol). The cloudy yellow solution is stirred at room temperature for 1 hour. The mixture is quenched with water and saturated NaHCO3 solution and extracted with CH2Cl2. The organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to a yellow oil. The oil is purified by column chromatography (5:95 methanol/ethyl acetate) to afford the title compound (1.08 g, 79% over 2 steps) as a white solid. Mp 53–54° C. 1H NMR (CDCl3, 400 MHz): δ 8.94 (br s, 1H), 7.83 (d, 1H), 7.18–7.13 (m, 2H), 6.98–6.94 (m, 1H), 6.62 (d, 1H), 6.38 (d, 1H), 4.38 (t, 2H), 3.16–3.02 (m, 4H), 2.76–2.60 (m, 4H), 2.55–2.46 (m, 2H), 1.90–1.82 (m, 2H), 1.77–1.64 (m, 2H). MS ES: m/z=462.72, 464.58.

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