Methyl iodide → N-(3-Aminopropyl)-N-methylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (0.82 g) in DMSO (20 ml) was added 2-(3-aminopropylamino)pyridine (4.7 g). The mixture was stirred and slowly heated under nitrogen to 85° C. After the evolution of hydrogen had ceased the mixture was cooled to room temperature and iodomethane (4.41 g) in DMSO (5 ml) added keeping the temperature below 35° C. After stirring for a further 30 minutes water (200 ml) was added and the resulting mixture extracted with chloroform. The extract was washed with water followed by 2N hydrochloric acid. The pH of the acid washings was raised to 14 (NaOH) and extracted again with chloroform. This final extract was dried (K2CO3) and stripped to an oil 3.84 g. Chromatography (silica gel, 10% ammoniacal methanol/dichloromethane) afforded 2-[N-(3-aminopropyl)-N-methylamino]pyridine 2.0 g (39%) as an oil.

Provenance & Evidence