N-(4,6-dimethyl-pyridin-2-yl)-N-methyl-3-[methyl-(4-nitro-phenyl)-amino]-propionamide → N-(4,6-dimethyl-pyridin-2-yl)-N,N'-dimethyl-N'-(4-nitro-phenyl)-propane-1,3-diamine

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Reaction Steps

Borane-dimethylsulfide complex (0.72 mL, 7.02 mmol) was added to a solution of N-(4,6-dimethyl-pyridin-2-yl)-N-methyl-3-[methyl-(4-nitro-phenyl)-amino]-propionamide (600 mg, 1.75 mmol) in tetrahydrofuran (10 mL) at 0° C. The mixture was warmed to room temperature then heated at reflux overnight. After cooling to room temperature the solvent was evaporated in vacuo. The residue was quenched into ice water, extracted with ethyl acetate then the organic phase was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography over silica gel (60-120 mesh) using 10% ethyl acetate in hexane as eluent afforded N-(4,6-dimethyl-pyridin-2-yl)-N,N′-dimethyl-N′-(4-nitro-phenyl)-propane-1,3-diamine (350 mg, 61%) as yellow semi solid.

Provenance & Evidence