[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:17]([CH:19]3[CH2:24][CH2:23][N:22](CC4C=CC=CC=4)[CH2:21][CH2:20]3)=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:17]([CH:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:32][CH:33]=1A solution of N1-(4-methoxybenzoyl)-N2-(1-benzylpiperidin-4-ylcarbonyl)-1,2-benzenediamine (1.02 g, 2.30 †mmol), 1 N aqueous hydrochloric acid (5 mL), and 5% pallidium-on-carbon (1.06 g) in ethanol (100 mL) was placed under a hydrogen atmosphere (1 bar). After 16 h, the mixture was filtered through diatomaceous earth and the filtrate concentrated in vacuo. The residue was treated with 1 N aqueous sodium hydroxide followed by ethyl acetate. The aqueous layer was extracted twice with ethyl acetate and the combined organics were washed with 1 N aqueous sodium hydroxide, saturated sodium chloride solution, and dried (potassium carbonate). Concentration and recrystallization yielded 656 mg (81%) of the title compound.
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