Hydrochloric Acid → N4-cyclohexylmethyl-2-fluoro-5-nitro-N1-phenyl-benzene-1,4-diamine

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Reaction Steps

A solution of 2,4-difluoro-5-nitro-N-phenylaniline (1.00 g, 4.00 mmol), cyclohexanemethylamine (0.57 mL, 4.40 mmol) and N,N′-diisopropylethylamine (0.77, 4.40 mmol) in DMF (40 mL) was stirred at room temperature under an inert atmosphere for 18.5 h. The reaction mixture was transferred to a separatory funnel containing 2 N HCl. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water, brine and dried over MgSO4. The solution was filtered through diatomaceous earth and the solvent was evaporated. The resulting dark red residue was flash chromatographed (10% EtOAc/hexanes) to give N4-cyclohexylmethyl-2-fluoro-5-nitro-N1-phenyl-benzene-1,4-diamine as a dark red solid (0.48 g, 34.9% yield). M+, 344

Provenance & Evidence