Diethyl Ether → 1-(4-Bromo-2-(methoxymethyl)phenyl)-2-methylpiperidine

Participants

Reaction Conditions

Reaction Steps

To a solution of solution of [5-bromo-2-(2-methylpiperidin-1-yl)phenyl]methanol (7.9 g; 27.8 mmol) and n-ethyldiisopropylamine (10.40 mL; 61.15 mmol) in anhydrous DCM (150 mL) cooled to 0° C., was added methanesulfonyl chloride (2.36 mL; 30.57 mmol). The reaction mixture was diluted with MeOH (150 mL) and heated to 50° C. for 3 h after which time solvents were removed under vacuum to give a brown oil. Residue was taken up with Et2O (450 mL), washed with water (150 mL, pH 8 adjusted with aqueous NaOH), saturated aqueous solution of NH4Cl (2×150 mL) and brine (150 mL). The combined organic layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure to give the title compound as a brown yellow oil (12.97 g, 92%). LC/MS (Method B): 298.1 (M+H)+.

Provenance & Evidence