Benzylamine → Benzyl(2,2-difluoroethyl)amine

HRID 2098414Notes

Reaction equation

HRID 2098414 reaction equation
[F:1][CH:2]([F:5])[CH2:3]Cl.[CH2:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O>[CH2:6]([NH:13][CH2:3][CH:2]([F:5])[F:1])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 2736499Chlorodifluoroethane (mixed isomers)

Product 1

HCID 50896648Benzyl(2,2-difluoroethyl)amineYield 93.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An amount of 757.9 g (7.39 mol) of 2,2-difluoro-1-chloroethane and 800 g of benzylamine (7.39 mol) are heated in an autoclave at an internal temperature of 120° C. for 16 hours. Subsequently, 1400 g of water are added and the aqueous phase is separated. The organic phase is distilled at standard pressure and the excess 2,2-difluoro-1-chlorethan is distilled off Remaining traces of 2,2-difluoro-1-chloroethane are distilled off under vacuum (200 mbar). An amount of 587 g of N-benzyl-2,2-difluoroethanamine is obtained as residue with a purity of 97.4%. This corresponds to a yield of 93.4%, based on reacted benzylamine. The benzylamine hydrochloride in the aqueous phase can be rereleased by addition of sodium hydroxide solution and be used once again. A further 21 g of N-benzyl-2,2-difluoroethanamine are present in the aqueous phase so that the yield is increased to 96%.

Workup

  1. customthe aqueous phase is separated
  2. distillationThe organic phase is distilled at standard pressure
  3. distillationthe excess 2,2-difluoro-1-chlorethan is distilled off
  4. distillationare distilled off under vacuum (200 mbar)

Sources & evidence

ORD record
ord-50c2b2e063854f12a61246da3170e8bf
Source dataset
uspto-grants-2013_05
Patent number
US08450528B2

Reaction notes

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