2,4-Diaminotoluene → N-(4-Methyl-3-aminophenyl)-4-(4-methylpiperazinomethyl)benzamide

Participants

Reaction Conditions

Reaction Steps

A solution of AlCl3 (1000 mg, 7.5 mmol) in toluene (3 ml) and acetonitrile (3.0 ml) at 0° C. under an atmosphere of argon is treated dropwise with a solution of 3-amino-4-methyl-aniline (470 mg, 6.0 mmol) in toluene (6 ml). The resulting brown solution is heated at 40° C. A solution of 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid methyl ester (745 mg, 3.0 mmol) in toluene (2 ml) is then added dropwise over a period of 30 min. The resulting mixture is stirred at 40° C. for 8 hrs and then cooled at 0° C. An aqueous saturated potassium-sodium tartrate (30 ml) and aqueous saturated NaHCO3 (40 ml) and t-butyl methyl ether (60 ml) are added sequentially. The organic phase is separated and washed with aqueous saturated NaCl. The aqueous phases are back-extracted with t-butyl methyl ether. The organic phases are combined, dried over MgSO4 and concentrated in vacuo. Purification by flash-chromatography (SiO2, CH2Cl2/MeOH 90:10+1% aq. NH3) gives 825 mg of the title compound (75%) as yellowish crystals.

Provenance & Evidence