2-Pyridinemethanamine → HCID 15295462, compound

Participants

Reaction Steps

To a magnetically-stirred suspension of 1,1'-carbonyldiimidazole (3.6 mmol, 0.583 g) in dry toluene (20 mL) at 0° C. was added neat 2-(aminomethyl)pyridine (3.6 mmol, 0.371 mL) dropwise over 10 min. The resulting suspension was stirred at room temperature for 30 minutes, then, heated to reflux for 1.25 hours. The oily solution was slowly cooled to room temperature, at which time a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)piperidine (1.8 mmol, 0.500 g) in toluene (5 mL) was added dropwise over 15 minutes. The resulting suspension was heated to reflux for 4 hours, and the homogenous solution was then cooled to room temperature. The solvent was removed in vacuo, the residue dissolved in EtOAc (200 mL) and washed with 1N NaOH (2×200 mL) and H2O (4×200 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (SiO2 : 1 ) EtOAc: 2) 50% EtOAc/MeOH: 3) MeOH) to afford the title compound as a yellow solid, mp=104°-105° C. (0.3 mmol. 0.121 g. 16% yield).

Provenance & Evidence