Reaction #1885021

Reaction equation

2-chloro-5-chloromethylpyridine

2,2-difluoroethan-1-amine

triethylamine

→

N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethan-1-amine

Yield 53.9%

Solvents

acetonitrile

Conditions

Workup

1. 1
   ConcentrationAfter concentrating the reaction mixture under reduced pressure, it
2. 2
   Washwashed with ethyl acetate
3. 3
   Extractionextracted repeatedly with ethyl acetate
4. 4
   ConcentrationConcentrating the organic phase under reduced pressure

Procedure

At 45° C., 41.57 g (256.6 mmol) of 2-chloro-5-chloromethylpyridine, 20.80 g (256.6 mmol) of 2,2-difluoroethan-1-amine and 35.8 ml (256.6 mmol) of triethylamine are stirred in 500 ml of acetonitrile for 21 hours. After concentrating the reaction mixture under reduced pressure, it is taken up with 1 N aqueous hydrochloric acid and washed with ethyl acetate. The aqueous phase is alkalized with 2.5 N aqueous sodium hydroxide solution and extracted repeatedly with ethyl acetate. Concentrating the organic phase under reduced pressure affords 28.6 g (53% of theory) of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethan-1-amine.

Source