N-Methylbenzylamine → Benzyl-methyl-(2-pyridine-3-yl-ethyl-)amine

Participants

Reaction Steps

To a solution of pyridine-3-yl-acetic acid hydrochloride (5 g), benzyl-methyl-amine (3.5 g), and benzotriazole-1-yloxytris-hydroxymethyl-aminomethane(dimethylamino) phosphonium hexafluorophosphate (14 g) in dichlorometan (50 mL) was added triethylamine (8.8 mL). After this solution was stirred for 15 minutes, the residue from the evaporation of the solvent at reduced pressure was purified by silica gel column chromatography (hexane/ethyl acetate), and a colorless oily matter was obtained. This oily substance was dissolved in a tetrahydrofuran solution (60 mL), added dropwise into an anhydrous tetrahydrofuran (300 mL) in which lithium aluminum hydride (2.1 g) was suspended, and stirred for 1 hour. To the reaction solution was added diethyl ether (60 mL), water (2.1 mL), an aqueous solution (2.1 mL) of 15% sodium hydroxide and water (6.3 mL). After stirring for 30 minutes, the resulting solid was removed by filtration, the residue from the removal of the solvent by evaporation was purified by NH silica gel column chromatography (hexane/ethyl acetate), and the oily residue (4.35 g) was obtained.

Provenance & Evidence