Triethylamine → N,N-dimethyl-2-nitrobenzylamine

To a stirred mixture of 4-(bromomethyl)-3-nitrobenzonitrile (5.00 g, 20.74 mmol) (prepared according to the method described in WO 07/024,945 A1) and dimethylamine hydrochloride (2.03 g, 24.89 mmol) in CH2Cl2 (70 mL) was added triethylamine (6.30 g, 62.23 mmol) dropwise at 0° C., and the mixture was stirred at room temperature overnight. The reaction mixture was evaporated to dryness under reduced pressure, and the residue was diluted with water (20 mL) and extracted with CH2Cl2 (3×100 mL). The CH2Cl2 solution was dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of EtOAc and hexane as eluent to give 4-((dimethylamino)methyl)-3-nitrobenzene (3.58 g, 84%) as an orange solid. 1H NMR (400 MHz, CDCl3): δ 8.15 (br s, 1H), 7.92 (br s, 1H), 7.85 (br d, 1H, J=7.2 Hz), 3.80 (s, 2H), 2.27 (s, 6 H).

1. customprepared
2. customThe reaction mixture was evaporated to dryness under reduced pressure
3. additionthe residue was diluted with water (20 mL)
4. extractionextracted with CH2Cl2 (3×100 mL)
5. dry with materialThe CH2Cl2 solution was dried over anhydrous Na2SO4
6. filtrationfiltered
7. customevaporated to dryness under reduced pressure
8. customThe residue was purified by MPLC on silica gel using
9. additiona mixture of EtOAc and hexane as eluent

ORD record

ord-7313c96c785642a7b7c79502fced8422

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080568B1