Triethylamine → HCID 66632964, compound

To a stirred mixture of 3-(bromomethyl)-5-nitrobenzonitrile (1.50 g, 6.22 mmol) (prepared according to the method described in J. Org. Chem. 55: 1040-1043 (1990)) and dimethylamine hydrochloride (1.01 g, 12.44 mmol) in CH2Cl2 (15 mL) was added triethylamine (1.88 g, 18.66 mmol) dropwise at 0° C. The resulting mixture was stirred at room temperature for 3 h and evaporated to dryness under reduced pressure. The residue was diluted with water (15 mL) and extracted with EtOAc (3×50 mL). The EtOAc 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 3-((dimethylamino)methyl)-5-nitrobenzonitrile (1.10 g, 87%) as a viscous liquid. 1H NMR (400 MHz, CDCl3): δ 8.45 (s, 1 H), 8.40 (d, 1H, J=1.6 Hz), 8.01 (s, 1H), 3.59 (s, 2H), 2.30 (s, 6H).

1. customprepared
2. customevaporated to dryness under reduced pressure
3. additionThe residue was diluted with water (15 mL)
4. extractionextracted with EtOAc (3×50 mL)
5. dry with materialThe EtOAc 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-c5f25957aca94923924263869fd38c62

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080568B1