Sodium Carbonate → 2-[1-(3,6-Dichloropyridazin-4-yl)piperidin-4-yl]ethan-1-ol

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Reaction Steps

To a 50 mL round bottom flask, 9.18 g (0.05 mol) of 3,4,6-trichloro-pyridazine, 5.30 g (0.05 mol) of anhydrous sodium carbonate and 20 mL of N,N-dimethylacetamide (DMA) were added, stirred at room temperature, then 6.54 g (0.05 mol) of 2-(piperidin-4-yl)-ethanol (dissolved in 10 mL DMA) was added dropwise slowly, after the dropwise addition, the agitation was kept overnight, the reaction liquid was poured into 100 mL of distilled water on the next day, extracted for three times by using total 200 mL of dichloromethane, the extract solutions were combined together, dried over anhydrous Na2SO4, concentrated, and separated by using column chromatograph (eluent, petroleum ether:acetone=10:3) to obtain 6 g of 2-[1-(3,6-dichloro-pyridazin-4-yl)-piperidin-4-yl]-ethanol, yield: 43.6%, 1H-NMR (400MHz, DMSO-D6) δppm: 1.21˜1.31(m, 2H), 1.39˜1.43(m, 2H), 1.59˜1.67(m, 1H), 1.76˜1.79(dbrs, 2H), 2.82˜2.88(dt, 2H, J=11Hz), 3.45˜3.49(m, 2H), 3.70˜3.73(dbrs, 2H), 4.40˜4.42(t, 1H, J=5Hz), 7.35(s, 1H).

Provenance & Evidence