Triethylamine → HCID 44212570, compound

Participants

Reaction Steps

4Bromophenylacetic acid (0.300 g, 1.40 mmol) was suspended in thionyl chloride (10 ml) and heated to reflux with stirring. After 1 h, the reaction mixture was allowed to cool and was evaporated under reduced pressure to give a yellow oil. The oil was then azeotroped with toluene, and the residue dried in vacuo to give the crude acid chloride. Meanwhile 4-methoxy-3-(4-methyl-1-piperazinyl)benzeneamine (EP 0533 267 A1) (0.293 g, 1.33 mmol) was dissolved in dichloromethane (10 ml) and treated with triethylamine (0.195 ml, 1.40 mmol), followed by dropwise addition of a solution of the crude acid chloride in dichloromethane (3 ml). The mixture was stirred at room temperature overnight before being washed with NaHCO3 solution. The organic layer was then dried (Na2SO4), and was evaporated under reduced pressure to give a brown oil. The oil was purified by silica-gel chromatography (5% MeOH/CH2Cl2 as eluant) to give the title compound as a pale yellow oil (0.295 g, 50%), which was converted to its oxalate salt.

Provenance & Evidence