N,N,N',N'-Tetramethylmethanediamine → HCID 19042884, compound

Participants

Reaction Steps

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.083 g, 0.11 mL, 0.812 mmol) in CH2Cl2 (2.4 mL) with acetyl chloride (0.064 g, 0.057 mL, 0.80 mmol) followed by a solution of 4-chloro-5-phenoxy indole (0.14 g, 0.574 mmol) in CH2Cl2 (2 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)4-chloro-5-phenoxyindole, as an off-white solid. This was treated with potassium cyanide (0.143 g, 2.19 mmol) and methyl iodide (0.0.33 g, 0.143 mL, 2.29 mmol) in DMF (1 mL) for 16 hr After appropriate work-up and chromatography (silica gel; hexane/Et2O; 0-55%), 3-cyanomethyl-4-chloro-5-phenoxyindole was obtained as an off-white crystalline solid, 0.094 g (58%).

Provenance & Evidence