Dimethylamine → HCID 13774679, compound

In a 250 mL round bottom flask was charged 1-(2-bromoethyl)-3-nitrobenzene (10 g, 43.5 mmol) and acetonitrile (36 mL). The suspension was treated with triethylamine (18.1 mL, 130 mmol) and dimethylamine (2 M in tetrahydrofuran, 65.2 mL, 130 mmol). The resulting mixture was stirred at ambient temperature for 48 hours. The mixture was concentrated. The residual solid was partitioned between ethyl acetate (130 mL) and 60 ml saturated aqueous sodium bicarbonate. The aqueous layer was washed with ethyl acetate (75 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The concentrate was purified by flash chromatography on an 80 g silica gel column using an AnaLogix IntelliFlash 280 system eluting with a gradient of from 0% to 7% methanol in CH2Cl2 to provide the title compound. MS (DCI(+)) m/e 195.1 (M+H)+.

1. concentrationThe mixture was concentrated
2. customThe residual solid was partitioned between ethyl acetate (130 mL) and 60 ml saturated aqueous sodium bicarbonate
3. washThe aqueous layer was washed with ethyl acetate (75 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe concentrate was purified by flash chromatography on an 80 g silica gel column
9. washeluting with a gradient of from 0% to 7% methanol in CH2Cl2

ORD record

ord-db99926c7ec5421787b4f25a9fbfb945

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354422B2