N,N,N',N'-Tetramethylmethanediamine → HCID 19042918, compound

Participants

Reaction Steps

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.829 g, 1.11 mL, 8.12 mmol) in CH2Cl2 (10 mL) with acetyl chloride (0.637 g, 0.573 mL, 8.12 mmol) followed by a solution of 5-(pyrid-3-yloxy)indole (1.23 g, 5.8 mmol) in CH2Cl2 (100 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)-5-(pyrid-3-yloxy)indole as a gum. This was treated with finely ground potassium cyanide (1.246 g, 19 mmol) and methyl iodide (2.7 g, 1.18 mL, 19 mmol) in DMF (70 mL) for 16 hr, and after appropriate work-up and chromatography (silica gel; hexane/EtOAc; 0-60%), 3-cyanomethyl-5-(pyrid-3-yloxy)indole was obtained a gum, which solidified on standing, 0.655 g (45%).

Provenance & Evidence