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

Temperature

60 °C

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.

1. temperatureto cool
2. customThe organics were collected
3. extractionthe product was extracted with 1N aqueous hydrogen chloride
4. customThe organics were removed
5. extractionThe product was extracted with dichloromethane (100 mL)
6. washwashed with saturated aqueous sodium chloride (200 mL)
7. dry with materialThe organics were dried over magnesium sulfate
8. customthe solvent removed at reduced pressure

ORD record

ord-c54cbcf8dd9c44a192b20de571407c7a

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622467B2