N-(2-Aminoethyl)piperidine → (4-Isopropyl-piperazin-1-yl)-[6-(2-piperidin-1-yl-ethylamino)-pyridin-3-yl]-methanone

Participants

Reaction Steps

(4-Isopropyl-piperazin-1-yl)-[6-(2-piperidin-1-yl-ethylamino)-pyridin-3-yl]-methanone. A solution of (6-chloro-pyridin-3-yl)-(4-isopropyl-piperazin-1-yl)-methanone (0.20 g, 0.75 mmol) and 1-(2-aminoethyl)-piperidine (0.16 mL, 1.13 mmol) in 1-butanol (10 mL) was heated at reflux temperature. After 18 h the reaction was concentrated, treated with 1 N aq. NaHCO3 (25 mL), and extracted with DCM (3×25 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the residue (SiO2: 2-5% 2 M NH3 in MeOH/DCM) gave the title compound as an oil (0.050 g, 20%). MS (ESI): exact mass calcd. for C20H33N5O, 359.3; m/z found, 360.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.20 (d, J=1.8, 1H), 7.54 (dd, J=8.6, 2.3, 1H), 6.40 (d, J=9.0, 1H), 5.49 (br s, 1H), 3.65 (br s, 4H), 3.39-3.35 (m, 2H), 2.74-2.70 (m, 1H), 2.59-2.57 (m, 2H), 2.53 (br s, 4H), 2.42 (br s, 4H), 1.62-1.56 (m, 4H), 1.46-1.45 (m, 2H), 1.04 (d, 6.5, 6H).

Provenance & Evidence