Piperidine → (4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanone

참여 물질

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(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanone. To a solution of 6-(4-isopropyl-piperazine-1-carbonyl)-pyridine-3-carbaldehyde (0.250 g, 0.96 mmol) and piperidine (0.11 mL, 1.10 mmol) in DCM (20 mL) was added NaB(OAc)3H (0.300 g, 1.44 mmol). After 18 h, 1 N NaOH (15 mL) was added and the mixture was extracted with DCM (3×25 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2: 4-8% 2 M NH3 in MeOH/DCM) gave the title compound as an oil (0.030 g, 9%). MS (ESI): exact mass calcd. for C19H30N4O, 330.2; m/z found, 331.5 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.49 (s, 1H), 7.77 (dd, J=7.8, 2.0, 1H), 7.58 (d, J=7.8, 1H), 3.82 (t, J=5.0, 2H), 3.61 (t, J=5.0, 2H), 3.49 (s, 2H), 2.75-2.72 (m, 1H), 2.62 (t, J=5.0, 2H), 2.51 (t, J=5.0, 2H), 2.37 (br s, 4H), 1.60-1.54 (m, 4H), 1.45-1.43 (m, 2H), 1.05 (d, J=6.6, 6H).

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