Toluene → HCID 18940669, compound

Participants

Reaction Steps

4-Chlorobenzoic acid (350 mg, 2.23 mmol) was heated at reflux with thionyl chloride (3 ml) and toluene (40 ml) for 2 h, and then evaporated to dryness under reduced pressure. 4-Methoxy-3-(4-methyl-1-piperazinyl)phenylamine (494 mg, 2.23 mmol) in dry dichloromethane (40 ml) was added with triethylamine (2 ml) and the mixture stirred for 1 h. The solution was partitioned between dichloromethane (40 ml) and saturated aqueous potassium carbonate (40 ml), the organic solution dried (sodium sulphate) and evaporated to dryness under reduced pressure to afford an oil, which was purified by column chromatography (silica, chloroform,/methanol 5%) to afford the title compound (774 mg, 97%) which was crystallised from methanol/diethyl ether as the oxalate salt.

Provenance & Evidence