C([O-])=O.[NH4+].C([N:12]1[CH2:17][CH2:16][C:15]([CH2:21][CH2:22][CH2:23][CH3:24])([N:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]1)C1C=CC=CC=1.CO.C(Cl)(Cl)[Cl:28]>CO.[OH-].[OH-].[Pd+2]>[ClH:28].[ClH:28].[CH2:21]([C:15]1([N:18]([CH3:20])[CH3:19])[CH2:16][CH2:17][NH:12][CH2:13][CH2:14]1)[CH2:22][CH2:23][CH3:24]1.5 g 20% Pd(OH)2/C and 6.95 g (3 eq) ammonium formate were added to a solution of 10 g (1 eq) 1-benzyl-4-butyl-N,N-dimethylpiperidin-4-amine in 100 ml MeOH. The reaction mixture obtained was refluxed for 30 min. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). Once the conversion was complete, the reaction solution was cooled to room temperature, filtered over celite and rewashed with methanol. The methanol is distilled off, the residue taken up in ethyl acetate/hexane, the solvent decanted off and toluene added. The organic phase thus obtained was concentrated under reduced pressure and the residue taken up in 150 ml dichloromethane. HCl gas was passed through the dichloromethane solution for 20 min, the solvent was distilled off and 7 g (74%) of product were obtained in this way as a white solid.
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