HCID 9795992, compound → HCID 57672014, compound

Participants

Reaction Steps

A solution of trans-1-[3-(4-acetylphenoxy)propyl]-3,5-dimethylpiperidine (289 mg) in tetrahydrofuran (1 mL) is stirred at room temperature under anhydrous atmosphere and a 2.61 M solution of methylmagnesium bromide in tetrahydrofuran (400 μL) is added dropwise. The mixture is stirred at room temperature for 3 h and quenched with a saturated aqueous solution of ammonium chloride. The solution is extracted with ethyl acetate and the combined extracts washed with water, dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with dichloro-methane/methanol 95/5 as eluent. Fractions containing the expected product are pooled and salted with 20 mg of oxalic acid to give 70 mg of trans-1-{3-[4-(1-hydroxy-1-methylethyl)-phenoxy]propyl}-3,5-dimethylpiperidine, oxalate as a pale yellow solid.

Provenance & Evidence