Piperidine → 2-Piperdin-1-ylmethyl-5-(3-piperdin-1-yl-propoxy)-pyridine

Participants

Reaction Steps

A solution of 5-(3-chloro-propoxy)-2-piperidin-1ylmethyl-pyridine (0.25 g, 0.86 mmol), piperidine (0.09 mL, 0.94 mmol), KI (0.003 g, 0.017 mmol), and Na2CO3 (0.045 g, 0.43 mmol) in 1-butanol (5 mL) was heated to 95° C. After 18 h the reaction mixture was concentrated, diluted with DCM (50 mL) and filtered through a pad of diatomaceous earth. The filtrate was concentrated and chromatography of the residue (SiO2: 3-8% 2 M NH3 in MeOH/DCM) gave the title compound as an oil (0.025 g, 10%). MS (ESI): exact mass calcd. for C19H31N3O, 317.3; m/z found, 318.5. 1H NMR (400 MHz, CDCl3): 8.23 (d, J=2.8, 1H), 7.29 (d, J=8.1, 1H), 7.16 (dd, J=8.6, 3.0, 1H), 4.03 (t, J=6.3, 2H), 3.55 (s, 2H), 2.48-2.40 (m, 10H), 2.01-1.96 (m, 2H), 1.61-1.46 (m, 8H), 1.43 (br s, 4H).

Provenance & Evidence