N,N,N',N'-Tetramethylmethanediamine → 3-Cyanomethyl-5-(4-methylphenoxy)indole

Participants

Reaction Steps

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.24 g, 0.32 mL, 2.35 mmol) in CH2Cl2 (7 mL) with acetyl chloride (0.19 g, 0.17 mL, 2.39 mmol) followed by a solution of 5-(4-methylphenoxy)indole (0.39 g, 1.74 mmol) in CH2Cl2 (6 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)-5-(4-methylphenoxy)indole as a gum. This was treated with potassium cyanide (0.43 g, 6.6 mmol) and methyl iodide (0.98 g, 0.43 mL, 6.9 mmol) in DMF (6 mL) for 16 hr, and after appropriate work-up, 3-cyanomethyl-5-(4-methylphenoxy)indole was obtained as an off-white crystalline solid 0.338 g (74%).

Provenance & Evidence