Dichloromethane → Carbazole, 9-(3-(dimethylamino)propyl)-

Participants

Reaction Steps

A 250-mL round-bottomed flask was charged with NaH (5.6 g, 140.00 mmol, 4.00 equiv, 60%) in DMF (100 mL). To this was added dimethylamine hydrochloride (4.23 g, 52.22 mmol, 1.50 equiv) in DMF (50 mL) at room temperature. To this mixture 9-(3-bromopropyl)-9H-carbazole (10 g, 34.70 mmol, 1.00 equiv) was added and the resulting mixture was stirred at room temperature for 4 hours. The reaction progress was monitored by TLC (DCM:MeOH=10:1). Upon completion, the reaction was then quenched by the addition of ice/salt (100 mL). The resulting mixture was extracted with ethyl acetate (3×50 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator affording 3-(9H-carbazol-9-yl)-N,N-dimethylpropan-1-amine as yellow oil (7.37 g, 80%).

Provenance & Evidence