Methyl iodide → HCID 19097131, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-(3-cyanopropyl)-2,5-dimethoxyaniline (46.2 g; 0.22 mol) in absolute ethanol (400 ml) were added iodomethane (47.7 g; 0.34 mol) and triethylamine (34.0 g; 0.34 mol). After stirring at 50° C. for 24 hours a further portion of iodomethane (47.7 g; 0.34 mol) was added to the reaction mixture, which was then heated at 50° C. for a further 24 hours. The reaction mixture was then cooled, diluted with water (500 ml) and extracted with dichloromethane (3×200 ml) and washed with water (2×400 ml). The resulting organic extract was dried (MgSO4), the solvent was then removed under reduced pressure to give a brown oil. The crude product was purified by flash chromatography, eluting first with hexane and subsequently increasing the polarity with dichloromethane. This procedure afforded the product as a colourless oil (26.8 g; 54%).

Provenance & Evidence