[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O.Cl.[OH-:18].[Na+].N1([CH2:26][NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)CCCCC1.[C:34](O)(=O)[CH3:35]>O>[N:9]1([CH2:8][C:7]2[CH:15]=[CH:16][C:4]([NH:1][CH:34]=[C:35]3[C:29]4[C:28](=[CH:33][CH:32]=[CH:31][CH:30]=4)[NH:27][C:26]3=[O:18])=[CH:5][CH:6]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]11-(4-Nitro-benzyl)-piperidine (0.5052 gms.) is suspended in 25 mL of a 1:1 (v:v) solution of acetic acid and water. The suspension is then treated with 45 mL of an ˜10 wt. % solution of TiCl3 in 20–30 wt. % HCl, dropwise. Over the course of the addition a color change from colorless to purple to black ensues. The reaction mixture is immersed in a 60° C. oil bath overnight following the addition of TiCl3. The reaction mixture is then cooled to room temperature and made basic with the addition of a 10% aqueous solution of NaOH. The basic reaction mixture is extracted with chloroform, and the organic layer is dried over anhydrous sodium sulfate. Following evaporation of the solvent the organic layer yields 0.333 gms. of piperidin-1-ylmethyl-phenylamine.
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