Hydrochloric Acid → Benzyl(2,2-difluoroethyl)amine

HRID 2098409Notes

Reaction equation

HRID 2098409 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.C(N(CC)CC)C.Cl>CN(C)C(=O)C>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 8471TriethylamineHCID 2736499Chlorodifluoroethane (mixed isomers)

Product 1

HCID 50896648Benzyl(2,2-difluoroethyl)amineYield 90.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

An amount of 10 g (92 mmol) of 2,2-difluoro-1-chloroethane, 5 g (46 mmol) of benzylamine and 5.2 g (51 mmol) of triethylamine are heated in 18.7 g of N,N-dimethylacetamide in an autoclave at an internal temperature of 120° C. for 6 hours. Subsequently, 100 g of 1N hydrochloric acid are added and the solvent is removed under vacuum. The residue is taken up in 30 ml of dichloromethane and adjusted to pH 8 with solid sodium hydrogencarbonate. The phases are subsequently separated and the aqueous phase is again extracted with 20 ml of dichloromethane. The organic phase is distilled. An amount of 7.1 g of N-benzyl-2,2-difluoroethanamine is obtained, which corresponds to a yield of 90%, based on benzylamine

Workup

  1. customthe solvent is removed under vacuum
  2. customThe phases are subsequently separated
  3. extractionthe aqueous phase is again extracted with 20 ml of dichloromethane
  4. distillationThe organic phase is distilled

Sources & evidence

ORD record
ord-61c5e0bf15144270b858ee819d2a6bcf
Source dataset
uspto-grants-2013_05
Patent number
US08450528B2

Reaction notes

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