HCID 71608063, compound → N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine

HRID 2044132Notes

Reaction equation

HRID 2044132 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:13][CH:14]([F:16])[F:15])CC=C)=[CH:4][CH:3]=1>C(O)CCC.[Pd]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:13][CH:14]([F:16])[F:15])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 71608063HCID 71608063, compound

Product 1

HCID 44604123N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamineYield 85.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 2631-ButanolSolvent

Procedure

An amount of 2 g (7.38 mmol) of N-[(6-chloropyridin-3-yl)methyl]-N-(2,2-difluoroethyl)prop-2-en-1-amine is placed in 20 ml of n-butanol and treated with 100 mg of 10% palladium-on-charcoal (water-moistened). The mixture is subsequently stirred and heated at reflux for 18 h until complete conversion has been achieved. The reaction mixture is cooled to ambient temperature and then filtered through celite. The solvent is removed under vacuum. An amount of 1.3 g of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine is obtained (corresponds to 84% yield).

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 h until complete conversion
  3. filtrationfiltered through celite
  4. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-fefdd8e6ba1c491fab8bdef71670b406
Source dataset
uspto-grants-2013_11
Patent number
US08586756B2

Reaction notes

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