[N+:1]([O-:4])(O)=[O:2].[NH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1>C(O)(=O)C>[N+:1]([C:16]1[CH:17]=[C:12]([CH2:11][CH:8]2[CH2:7][CH2:6][NH:5][CH2:10][CH2:9]2)[CH:13]=[CH:14][C:15]=1[OH:18])([O-:4])=[O:2]Concentrated nitric acid in acetic acid (8 mL 70% HNO3 aq in 16 mL acetic acid) was added slowly to a stirred solution of 4-(piperidin-4-ylmethyl)phenol (Guzikowski et al, J. Med Chem., 2000, 43, 984–994) (100 mmol) in acetic acid (300 mL) and the resultant slurry stirred at 80° C. for 1 h. The reaction mixture was then filtered and evaporated in vacuo to give the title compound as a brown solid.
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