Sodium hydride → 4-[2-[(5-Bromo-3-pyridyl)methoxy]ethyl]morpholine

Participants

Reaction Conditions

Reaction Steps

To the NaH (484 mg, 60% in mineral oil, 12.1 mmol) in DMF (dry, 1 mL) at 0° C., is slowly added 2-morpholin-4-yl-ethanol (1.47 ml, 12.1 mmol). Then the mixture is stirred at 0° C. for 30 min. 3-bromo-5-chloromethyl-pyridine (500 mg, 2.42 mmol) is added at 0° C. The mixture is then stirred at room temperature overnight and is quenched by adding water dropwise. The mixture is partitioned between DCM and water. The DCM phase is separated and then washed with water twice. The DCM phase is evaporated under high vacuum. The residue is separated by silica gel flash column (MeOH/DCM 0 to 5% gradient, then 5%) to obtain 370 mg of 4-[2-[(5-bromo-3-pyridyl)methoxy]ethyl]morpholine.

Provenance & Evidence