Hydrogen iodide → 3-Chloro-5-methoxy-4-piperidin-1-ylmethylphenol

Participants

Reaction Conditions

Reaction Steps

Hydroiodic acid (57% solution, 5 mL) was added to 1-(2-chloro-4,6-dimethoxybenzyl)-piperidine (360 mg, 1.3 mol) and the mixture heated at 60° C. for 2 h. The reaction mixture was cooled to ambient temperature, diluted with saturated aqueous sodium carbonate solution (20 mL) and extracted with DCM (3×30 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford an beige solid that was then purified by flash chromatography (silica, 12 g column, ISCO, 0-15% (2N ammonia in methanol) in DCM) to afford the title compound as a white solid (277 mg, 88%). 1H NMR (CDCl3, 400 MHz): 6.08 (d, J=2.2 Hz, 1H), 5.96 (d, J=2.2 Hz, 1H), 3.61 (s, 3H), 3.59 (s, 2H), 3.31 (br s, 1H), 2.74-2.64 (m, 4H), 1.70-1.62 (m, 4H), 1.60-1.43 (m, 2H).

Provenance & Evidence