Morpholine → N-(5-Amino-pyridin-2-yl)-2-piperidin-1-yl-acetamide

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Reaction Steps

Compound 20 (3.0 g, 13.9 mmol), was dissolved in THF (100 mL). Morpholine (20 mL, 229 mmol) was added and the mixture stirred at reflux for 1 hour. DCM (200 mL) and saturated aqueous sodium bicarbonate solution (200 mL) were added and the layers separated. The organic phase was dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was dissolved in EtOH (200 mL) and 10% Pd/C (wet, ˜300 mg) followed by ammonium formate (880 mg, 14.0 mmol) added. The mixture was stirred at reflux for 1 hour. The mixture was cooled to rt, filtered through celite, washing the precipitate with EtOAc. The collected filtrate was diluted with saturated ammonium bicarbonate solution (100 mL) and the layers separated. The organic phase was dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was triturated with EtOAc-isohexane to afford the title compound as an off-white solid (2.1 g, 63%); (m/z): 237 [MH]+.

Provenance & Evidence