N,N,N',N'-Tetramethylmethanediamine → HCID 19042913, compound

Reaction equation

CN([CH2:4][N:5]([CH3:7])[CH3:6])C.C(Cl)(=O)C.[Br:12][C:13]1[CH:28]=[CH:27][C:16]([O:17][C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][CH:22]=[CH:21]3)=[CH:15][CH:14]=1>C(Cl)Cl>[CH3:7][N:5]([CH2:4][C:22]1[NH:23][C:24]2[C:20]([CH:21]=1)=[CH:19][C:18]([O:17][C:16]1[CH:27]=[CH:28][C:13]([Br:12])=[CH:14][CH:15]=1)=[CH:26][CH:25]=2)[CH3:6]

Participants

Procedure

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.186 g, 0.25 mL, 1.83 mmol) in CH2Cl2 (10 mL) with acetyl chloride (0.143 g, 0.13 mL, 1.83 mmol) followed by a solution of 5-(4-bromophenoxy)indole (0.394 g, 1.37 mmol) in CH2Cl2 (5 mL), gave after work-up 2-(N,N-dimethylaminomethyl)-5-(4-bromophenoxy)indole as a brown gum. This was treated with finely ground potassium cyanide (0.34 g, 5.21 mmol) and methyl iodide (0.77 g, 0.34 mL, 5.44 mmol) in DMF (30 mL) for 16 hr, and after appropriate work-up, 3-cyanomethyl-5-(4-bromophenoxy)indole was obtained as a brown gum 0.29 g, (ca 65%; carried through to next stage without further purification).