C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([Cl:23])[N:18]=2)[CH3:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[H][H]>[Pd].C(O)C.C([O-])(=O)C.[Na+]>[ClH:23].[N:20]1[CH:21]=[CH:22][C:17]([N:15]([CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH3:16])=[N:18][CH:19]=1A suspension of 1-t-butoxycarbonyl-4-{[(2-chloropyrimidin-4-yl)(methyl)amino]methyl}piperidine (3.00 g, 8.80 mmol) and 5% palladium on activated carbon (1.87 g, 0.880 mmol) in ethanol (70 mL) and 1N sodium acetate solution (17.6 mL) is stirred rapidly under 1 atmosphere of hydrogen for 2 hours. After the atmosphere of hydrogen is replaced with argon the mixture is filtered through a bed of Celite™ and ethyl acetate, water and saturated sodium bicarbonate are added to the solution. The phases are separated and the aqueous phase is extracted into ethyl acetate (×3). The combined organic extracts are dried (sodium sulfate), filtered and concentrated in vacuo. The residue is taken into methanol (270 mL) and hydrogen chloride gas is passed through the solution maintaining <20° C. The mixture is kept at this temperature for 2 hours before it is concentrated in vacuo and freeze-dried from water providing 4-{[(pyrimidin-4-yl)(methyl)amino]methyl}piperidine hydrochloride (2.63 g, 100%).
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