N,N,N',N'-Tetramethylmethanediamine → HCID 19042901, compound

Participants

Reaction Steps

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.26 g, 0.34 mL, 2.50 mmol) in CH2Cl2 (7.3 mL) with acetyl chloride (0.20 g, 0.18 mL, 2.53 mmol) followed by a solution of 5-(3-trifluoromethylphenoxy) indole (0.50 g, 1.79 mmol) in CH2Cl2 (6.2 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)-5-(3-trifluoromethylphenoxy)indole as a gum. This was treated with finely ground potassium cyanide (0.45 g, 6.9 mmol) and methyl iodide (1.03 g, 0.45 mL, 7.26 mmol) in DMF (9 mL) for 16 hr, and after appropriate work-up and chromatography (silica gel; hexane/Et2O; 0-45%) 3-cyanomethyl-5-(3-trifluoromethylphenoxy)indole was obtained as an almost colourless gum, 0.415 g (73%).

Provenance & Evidence