Hydrochloric Acid → 1-benzyl-N-methylpiperidin-4-amine

Participants

Reaction Steps

To a solution of 1-benzyl-4-piperidone (1.9 g, 10 mmol) in MeOH (10 ml) were added methylamine (8 ml, 16 mmol) and 3 Å molecular sieves. After stirring at RT for 1 h, the reaction was cooled in an ice-bath and 4N HCl in dioxane (2.5 ml, 10 mmole) and NaCNBH3 (1.2 g, 20 mmol) were added. The reaction was stirred at RT overnight. After the reaction was complete, H2O was added the pH was adjusted to 10 with 50% NaOH solution. The product was extracted with EtOAc (100 ml, 3×)from aqueous solution and combined. The combined organic solution was washed with brine, dried over MgSO4, filtered and concentrated to give an oil which was purified by silica flash chromatography, eluting with 8% saturated NH3 /MeOH in CH2Cl2 to give 4-methylamino-1-benzyl piperidine (1.77 g, 8.66 mmol, 86%). FAB Mass [M+1]+35Cl 205.

Provenance & Evidence