Triethylamine → HCID 66632208, compound

To a stirred solution of 3-(bromomethyl)-5-nitrobenzonitrile (1.50 g, 6.22 mmol) and pyrrolidine (0.53 g, 7.46 mmol) in CH2Cl2 (15 mL) was added triethylamine (1.88 g, 18.68 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 (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-nitro-5-(pyrrolidin-1-ylmethyl)benzonitrile (1.30 g, 90%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 8.45 (br s, 1H), 8.39 (br t, 1H, J=1.6 Hz), 8.02 (br s, 1H), 3.78 (s, 2H), 2.56 (br s, 4H), 1.84 (br s, 4H).

1. customThe reaction mixture was evaporated to dryness under reduced pressure
2. additionthe residue was diluted with water (15 mL)
3. extractionextracted with EtOAc (3×50 mL)
4. dry with materialThe EtOAc solution was dried over anhydrous Na2SO4
5. filtrationfiltered
6. customevaporated to dryness under reduced pressure
7. customThe residue was purified by MPLC on silica gel using
8. additiona mixture of EtOAc and hexane as eluent

ORD record

ord-2ca582a7aff64bf4befc4925f9f6bdab

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080568B1