1-Methylisonipecotamide (6.75g, 47. 5MMOLES) was dissolved in anhydrous THF (350mL), and the resulting mixture was added in portions to a stirred slurry of lithium aluminum hydride (1.8g, 47. 5mmoles) in anhydrous THF (100 mL) at 0 ℃ under nitrogen. The mixture was stirred at 0 ℃ for 30min and then heated at 66 ℃ for 25h under nitrogen. Distilled water (1.88 mL) was added dropwise to the stirred mixture at 0 ℃, followed by 20 percent aqueous sodium hydroxide (1.42 mL), and then distilled water (6.75mL), and the mixture was stirred for 15 min. The mixture was filtered, and the solids were washed with THF and dichloromethane. The combined filtrates were evaporated to dryness and chromatographed on a silica gel column (30x5 cm) using 15 percent-20 percent (10 percent CONC. ammonium hydroxide in METHANOL)-DICHLOROMETHANE as the eluant to give (1-Methyl-4-piperidinyl)methanamine (0.678g, 11percent).
