1-Benzylpiperidin-4-ol → HCID 11653839, compound

Participants

Reaction Steps

To a mixture of 6-chloropyridazine-3-carboxylic acid pentylamide (0.530 g, 2.33 mmol) and 1-benzylpiperidin-4-ol (0.399 g, 2.33 mmol) in dioxane (20 mL) was added KOtBu (0.288 g, 2.56 mmol). The colourless reaction mixture turned to bright red upon the addition of KOtBu. The reaction mixture was stirred at room temperature for 16 hours, then concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water, dried over Na2SO4, filtered and concentrated. The crude material was purified by column chromatography to afford the title compound in 28% yield (0.100 g). The solid material was triturated with ether give 22.7 mg of product as a colourless solid. M.p. 127-130° C. 1H NMR (300 MHz, CDCl3) δ 8.15 (d, J=9.3 Hz, 1H), 7.91 (t, J=5.1 Hz, 1H), 7.31 (m, 5H), 7.02 (d, J=9.3 Hz, 1H), 5.34 (septet, J=4.5 Hz, 1H), 3.51 (s, 2H), 3.44 (q, J=6.9 Hz, 2H), 2.79-2.73 (m, 2H), 2.35-2.27 (m, 2H), 2.15-2.09 (m, 2H), 1.93-1.83 (m, 2H), 1.62-1.54 (m, 2H), 1.36-1.29 (m, 4H), 0.89-0.85 (m, 3H). 13C NMR (75 MHz, CDCl3) δ 165.9, 162.5, 148.6, 138.4, 129.6, 129.1, 128.7, 128.3, 127.1, 118.6, 73.8, 62.9, 50.8, 39.5, 30.8, 29.2, 29.1, 22.4, 14.0. MS (ES+) m/z 363 (M+1).

Provenance & Evidence