Triethylamine → N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine

HRID 1797839Notes

Reaction equation

HRID 1797839 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[F:10][CH:11]([F:14])[CH2:12][NH2:13].C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][NH:13][CH2:12][CH:11]([F:14])[F:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1362742,2-DifluoroethanamineHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 44604123N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamineYield 53.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure, it
  2. washwashed with ethyl acetate
  3. extractionextracted repeatedly with ethyl acetate
  4. concentrationConcentrating the organic phase under reduced pressure

Sources & evidence

ORD record
ord-ea1ab50375b34e25b281175bbcaebf43
Source dataset
uspto-grants-2013_01
Patent number
US08343893B2

Reaction notes

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