[Synthesis]
3-(Di-tert-butoxymethylamino)-1-methylpiperidine (500 mg, 1.52 mmol) was used as raw material and dissolved in a 1,4-dioxane solution (19.75 mL) of methanol (7.5 mL) and 10% (v/v) concentrated sulfuric acid. The reaction mixture was stirred at 25°C for 0.5 hours. Methanol (300 mL) was then added and BioRad AG1-X8 resin (OH type) was added until the pH reached 10. The resin was removed by filtration and the resin was washed with methanol (2 x 200 mL). The eluates were combined and evaporated to dryness, and the residue was purified by silica gel column chromatography (30 × 2.5 cm) to afford 3-(aminomethyl)-1-methylpiperidine (69.2 mg, 35%) using 10% concentrated ammonium hydroxide in methanol solution-dichloromethane as eluent. The product characterization data were as follows: FABMS: m/z 129.1 (MH+); HRFABMS: m/z 129.1392 (MH+), calculated value C7H17N2: m/z 129.1392; 1H NMR (CDCl3) δ 0.90 (2H, m, CH2), 1.65 (2H, m, CH2), 1.72 (1H, m. CH), 1.79 (1H, m, CH2), 1.91 (1H, m, CH2), 2.30 (3H, s, NCH3), 2.64 (2H, m, CH2), 2.82 (1H, m, CH2NH2), 2.92 (1H, m, CH2NH2); 13C NMR (CDCl3) δ CH3: 46.7; CH2: 25.2, 28.0, 46.0, 36.4, 60.3; CH: 39.9. |