Sodium Cyanide → (4-Methyl-1H-indol-3-yl)acetonitrile

Participants

Reaction Steps

Trimethyl-(4-methyl-1H-indol-3-ylmethyl)-ammonium iodide (2.6 g, 7.5 mmol) is suspended in ethanol (53 mL) and sodium cyanide (736 mg, 15 mmol), is added to the reaction. The reaction is stirred and heated to reflux overnight. After 16 hours the reaction is cooled to room temperature and evaporated in vacuo. The resulting oil is taken up in dichloromethane and washed with water 3×, dried (Na2SO4), filtered and evaporated in vacuo. The resulting material is purified on silica with hexanes/dichloromethane as the eluent (1.0 g, 5 mmol, 71%) LC/MS (M++1): 171.3.

Provenance & Evidence