Pyridine → N1-(4-methoxybenzoyl)-N2-[1-(tert-butoxycarbonyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamine

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Reaction Steps

A solution of 1.9 M phosgene in toluene (2.0 mL) was treated with 1-(tert-butoxycarbonyl)-4-hydroxymethylpiperidine (200 mg, 0.930 mmol). After 1 h, the mixture was concentrated in vacuo and the residue dried under high vacuum for 4 h. The residue was dissolved in methylene chloride (2.5 mL) and then added dropwise to a solution of N1-(4-methoxybenzoyl)-1,2-benzenediamine (230 mg, 0.950 mmol) and pyridine (0.4 mL) in methylene chloride (5 mL) and tetrahydrofuran (1 mL). After 16 h, the mixture was poured into a mixture of water and ethyl acetate. The organic layer was washed once with 1.0 N aqueous hydrochloric acid, once with saturated sodium chloride solution, dried (potassium carbonate), and filtered. Concentration and purification of the residue by flash chromatography (silica gel, ethyl acetate/hexanes) yielded 416 mg (93%) of the title compound.

Provenance & Evidence