Ethyl chloroformate → HCID 11537578, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-((4-phenylpiperazin-1-yl)methyl)-phenylcyclopropanecarboxylic acid (1.0 g) and triethylamine (0.42 ml) in tetrahydrofuran (70 ml) was added ethyl chlorocarbonate (0.29 ml) under ice-cooling and the mixture was stirred at 0° C. for 1 hr and 20 min. To this solution was added a solution of sodium azide (0.2 g) in water (3 ml) under ice-cooling, and the mixture was stirred for 30 min and left standing overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a brown oil. The oil was dissolved in benzene (20 ml) and refluxed under heating for 40 min. The reaction mixture was ice-cooled and methylmagnesium bromide (3M, tetrahydrofuran solution) (0.93 ml) was added dropwise. The mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a colorless oil. The oil was subjected to silica gel column chromatography (developing solvent; ethyl acetate:methanol=20:1) to give a white solid. This solid was recrystallized from ethyl acetate-isopropyl ether to give the title compound (0.52 g) as white crystals, m.p.=129-139.5° C.

Provenance & Evidence