Triethylamine → 6-Chloro-N,N-dimethylnicotinamide

Temperature

0 °C

6-Chloronicotinoyl chloride (500 mg, 2.76 mmol) and triethylamine (0.576 ml, 4.13 mmol) were taken-up in THF (13.8 ml) under argon and cooled to 0° C. Dimethylamine hydrochloride (337 mg, 4.13 mmol) was dissolved in THF (2 ml) and added dropwise to the reaction mixture over 15 minutes. The mixture was maintained at 0° C. for 1 hour, warmed to room temperature, and stirred for 15 minutes. The reaction was then diluted with ethyl acetate and washed twice with brine. The aqueous layers were combined and back-extracted twice with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound.

1. additionadded dropwise to the reaction mixture over 15 minutes
2. temperatureThe mixture was maintained at 0° C. for 1 hour
3. temperaturewarmed to room temperature
4. washwashed twice with brine
5. extractionback-extracted twice with ethyl acetate
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-23012539da534a8f8942327a00bc1cc0

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2