Water → 2-[N-(3-aminopropyl)-N-propylamino]pyridine

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Reaction Steps

Sodium hydride (1.14 g) was dissolved in dimethylsulphoxide (DMSO) (20 ml) at 70°-75° C. The solution was cooled and 2-(3-aminopropylamino)pyridine (6.57 g) in DMSO (20 ml) was added at room temperature. N-Propyl iodide (8.13 g) in DMSO (10 ml) was added dropwise maintaining the temperature at 20°-25° C. After allowing the mixture to stand overnight, water (250 ml) was added and this mixture was extracted with ether. The ether extracts were washed with hydrochloric acid (2N) and the aqueous layers made alkaline to pH 10.5. The aqueous layer was extracted with ether and chloroform. The pH was adjusted to pH 14 and the aqueous layer was extracted again with ether. The final ether extract was dried (K2CO3O, and the ether was evaporated to give 2-[N-(3-aminopropyl)-N-propylamino]pyridine (3.4 g) as an oil which was used without further purification.

Provenance & Evidence