[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][N:16](C)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:20].[H][H]>C(O)C.[Pd]>[ClH:20].[ClH:20].[CH3:1][N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:10][CH2:9]13-Benzyl-9-methyl-3,9-diaza-spiro[5.5]undecane (Rice, L. M. et al. J Heterocyclic Chem. 1964, 1, 3, 125.) (1.2 g, 4.65 mmol) was dissolved in ethanol (20 mL). To this solution was added hydrochloric acid (4 N in dioxane, 3 mL) and palladium (10% on charcoal, 500 mg). The reaction was shaken on a Parr shaker overnight under 60 psi of hydrogen. The reaction mixture was filtered through a pad of celite, concentrated, and the residue treated with a mixture of ethyl acetate and hexanes, to yield 670 mg (60%) as a white powder. 1H-NMR (CD3OD) δ 1.68-1.72 (m, 4H), 2.88 (s, 3H), 3.16-3.22 (m, 6H), 3.38 (m, 2H). Mass spec.: 169.12 (MH)+.
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