Dimethylformamide → Tert-butyl 4-(4-{2-[(6-methylpyridin-2-yl)oxy]ethyl}benzyl)piperazine-1-carboxylate

Participants

Reaction Steps

To a DMF (10 mL) solution of tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate (1.000 g) was added NaH (112 mg, 60% in mineral oil) at 0° C., then the resultant mixture was stirred for 1 hour. To the mixture was added 2-fluoro-6-methylpyridine (0.419 mL), then the resultant mixture was stirred at 70° C. over night. The mixture was poured into water, and extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=4/1 to 1/1) to afford tert-butyl 4-(4-{2-[(6-methylpyridin-2-yl)oxy]ethyl}benzyl)piperazine-1-carboxylate as a pale yellow amorphous powder (350 mg).

Provenance & Evidence