C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][C:10]([CH2:20][NH:21][CH:22]([CH3:24])[CH3:23])([NH:12]CC3C=CC=CC=3)[CH2:9]2)C=CC=CC=1.[ClH:31].O1CCOCC1>CO.[OH-].[Pd+2].[OH-]>[ClH:31].[CH3:23][CH:22]([NH:21][CH2:20][C:10]1([NH2:12])[CH2:11][NH:8][CH2:9]1)[CH3:24]To a solution of the 1-(diphenylmethyl)-3-{[(1-methylethyl)amino]methyl}-N-(phenylmethyl)azetidin-3-amine (0.35 g, 0.88 mmol) in methanol was added a solution of hydrogen chloride in dioxane (4 molar solution, 0.96 mL, 4.40 mmol) and the resulting mixture was concentrated to give a white solid which was taken back into methanol. To this solution were added palladium hydroxide (20% on carbon, 0.50 g, 0.19 mmol) and the resulting mixture shaken at 50 psi in a Parr apparatus for 3 h. The reaction mixture was filtered and concentrated to give a solid, which was washed with ether and dried in vacuo to give 3-{[(1-methylethyl)amino]methyl}azetidin-3-amine hydrochloride as a white solid (0.18 g, 81% yield). MS (EI) for CH17N3: 144 (MH+).
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