Methyl iodide → 4-(Dimethylamino)-N,N,N-trimethylanilinium iodide

Participants

Reaction Steps

N,N,N′,N′-Tetramethyl-benzene-1,4-diamine (200 mg, 1.22 mmol) was dissolved in dichloroethane (2 mL) and methyl iodide (173 mg, 1.22 mmol) was added dropwise. The reaction was refluxed for 1 hour, cooled to room temperature, the solid filtered out, washed with dichloromethane, dissolved in methanol and purified via flash column chromatography using a gradient of 0-8% MeOH:DCM to give 260 mg of grey solid (70% yield). 1H NMR (DMSO-d6): δ7.67 (d, J=9.3, 2H), 6.77 (d, J=9.3, 2H) 3.49 (s, 9H), 2.92 (s, 6H); MS (ESI, m/z): 179 (M+).

Provenance & Evidence