Methyl iodide → HCID 55248401, compound

To a stirred solution of 3-(2,2-diethoxyethylamino)benzonitrile (0.84 g, 3.59 mmol) in anhydrous DMF (5 mL) at 0° C. was added NaH (0.10 g, 4.30 mmol) portionwise. After 20 min, MeI (0.61 g, 4.30 mmol) was added, and the mixture was stirred at room temperature for 6 h. The reaction mixture was cooled to 0° C., and to it, aqueous NH4Cl (10 mL) solution was added dropwise. The aqueous mixture was extracted with CHCl3 (2×30 mL), and the organic phase 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-((2,2-diethoxyethyl)(methyl)amino)benzonitrile (0.65 g, 73%) as a viscous liquid. 1H NMR (400 MHz, CDCl3): δ 7.28-7.24 (m, 1H), 6.96-6.93 (m, 3H), 4.60 (t, 1H, J=5.2 Hz), 3.76-3.69 (m, 2H), 3.55-3.47 (m, 2H), 3.46 (d, 2H, J=5.2 Hz), 3.02 (s, 3H), 1.20 (t, 6H, J=7.0 Hz).

1. temperatureThe reaction mixture was cooled to 0° C.
2. extractionThe aqueous mixture was extracted with CHCl3 (2×30 mL)
3. dry with materialthe organic phase was dried over anhydrous Na2SO4
4. filtrationfiltered
5. customevaporated to dryness under reduced pressure
6. customThe residue was purified by MPLC on silica gel using
7. additiona mixture of EtOAc and hexane as eluent

ORD record

ord-8f5c41444d5548f6a3f53bb91974971b

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080568B1