Water → Methyl [4-({[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}amino)phenoxy]acetate

Participants

Reaction Steps

A suspension of 4-(2-tert-butylphenyl)-N-(4-hydroxyphenyl)piperazine-1-carboxamide (Example 174, 0.290 g, 0.82 mmol), methyl bromoacetate (0.163 g, 1.07 mmol), and potassium carbonate (0.227 g, 1.64 mmol) in DMF (3 mL) was stirred at room temperature for 24 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3 solution and brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to give the crude product, which was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 50:50) to provide methyl [4-({[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}amino)phenoxy]acetate (0.260 g, 75%) as a white powder.

Provenance & Evidence