Sodium Hydroxide → 3-(1-Methyl-4-piperidinyl)benzenamine

Participants

Reaction Steps

To a solution of 1-methyl-4-(3-nitrophenyl)pyridinium iodide (D5, 4.0 g, 11.7 mmol) in ethanol (100 ml) and water (100 ml) at 0° C. was added sodium borohydride (665 mg, 17.6 mmol) portionwise over 0.5 h, before allowing to warm to room temperature while stirring for 2h. To the mixture was added 10% NaOH solution (100 ml) and the product extracted with dichloromethane (2×), dried (Na2SO4) and evaporated in vacuo to a brown oil (2.6 g). The oil was dissolved in ethanol (100 ml) and hydrogenated over 10% Pd--C at 50 psi and 50° C. for 48 h. Filtration and evaporation in vacuo of the filtrate gave the title compound as a yellow oil (2.1 g, 93%).

Provenance & Evidence