Benzylamine → Benzyl(2,2-difluoroethyl)amine

HRID 2098413Notes

Reaction equation

HRID 2098413 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 768.1 g (7.39 mol) of 2,2-difluoro-1-chloroethane and 400 g of benzylamine (3.695 mol) are heated in an autoclave at an internal temperature of 120° C. for 16 hours. Subsequently, 700 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-chloroethane is distilled off. Remaining traces of 2,2-difluoro-1-chloroethane are distilled off under vacuum (200 mbar). An amount of 304 g of N-benzyl-2,2-difluoroethanamine is obtained as residue with a purity of 97.2%. 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.

Workup

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

Sources & evidence

ORD record
ord-7ebc519e4f794a9fb0dce63c23ba78e5
Source dataset
uspto-grants-2013_05
Patent number
US08450528B2

Reaction notes

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