Dichloromethane → n,n-Dimethyl-2-(4-nitrophenyl)ethanamine

Participants

Reaction Conditions

Reaction Steps

Dimethylamine hydrochloride (0.390 g, 4.78 mmol) was added to a solution containing 4-nitrophenethyl bromide (1.0 g, 4.35 mmol) and N,N-diisopropylethyamine (1.69 g, 13.05 mmol) in anhydrous dimethylformamide (20 mL). The reaction mixture was heated to 60° C. for 5 hours, then allowed to cool. The solution was diluted with 1:1 water:dichloromethane (200 mL), then added to a separatory funnel. The organics were collected and the product was extracted with 1N aqueous hydrogen chloride. The organics were removed and the aqueous layer was made basic with 1N aqueous sodium hydroxide. The product was extracted with dichloromethane (100 mL) and washed with saturated aqueous sodium chloride (200 mL). The organics were dried over magnesium sulfate and the solvent removed at reduced pressure to afford the title intermediate (0.426 g crude) as a clear oil, which was used without further purification.

Provenance & Evidence