Triphenylphosphine → HCID 86624203, compound

Participants

Reaction Steps

To a 50 mL dry three-necked flask, 0.554 g (0.002 mol) of self-made 2-[1-(3,6-dichloro-pyridazin-4-yl)-piperidin-4-yl]-ethanol, 0.20 g (0.002 mol) of p-hydroxybenzonitrile, 0.612 g of triphenylphosphine were added, 15 mL of anhydrous tetrahydrofuran was added under conditions of ice bath and nitrogen gas protection, then 0.35 mL of diethyl azodiformate (DEAD) dissolved in 5 mL of anhydrous tetrahydrofuran, was added dropwise into the flask. After the dropwise addition, the temperature was elevated to room temperature, the agitation was kept overnight. On the next day, the solvent was removed by evaporation using a rotation evaporator, the residue was poured into 100 mL of water, extracted for three times by using total 150 mL of dichloromethane, the extract solutions were combined together, dried over anhydrous Na2SO4, concentrated, and separated by column chromatograph (eluent, petroleum ether:ethyl acetate:methanol=10:3:0.1) to obtain 0.26 g of 4-{2-[1-(3,6-dichloro-pyridazin-4-yl)-piperidin-4-yl]-ethoxy}-benzonitrile, a white solid. Yield: 34.0%, m.p. 138˜139° C. 1HNMR (400MHz, CDCl3) δppm: 1.49˜1.55(m, 2H), 1.83˜1.86(m, 3H), 1.91˜1.94(dbrs, 2H), 2.82˜2.87(dt, 2H, J=11.4Hz), 3.76˜3.79(dbrs, 2H), 4.08˜4.11(t, 2H, J=5.8Hz), 6.85(s, 1H), 6.94˜6.96(d, 2H, J=8.8Hz), 7.58˜7.61(d, 2H, J=8.8Hz), 7.40(s, 1H).

Provenance & Evidence