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

HRID 2098411Notes

Reaction equation

HRID 2098411 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.[Br-].[K+].C(N(CC)CC)C.Cl>CN1CCCC1=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

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 8471TriethylamineHCID 253877Potassium BromideHCID 2736499Chlorodifluoroethane (mixed isomers)

Product 1

HCID 50896648Benzyl(2,2-difluoroethyl)amineYield 94%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

An amount of 10 g (92 mmol) of 2,2-difluoro-1-chloroethane, 5 g (46 mmol) of benzylamine, 1 g of potassium bromide and 5.2 g (51 mmol) of triethylamine are heated in 20.6 g of N-methylpyrrolidone 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 7.4 g of N-benzyl-2,2-difluoroethanamine is obtained, which corresponds to a yield of 94%, 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-58bc7628af54422ca3b3108c9977445c
Source dataset
uspto-grants-2013_05
Patent number
US08450528B2

Reaction notes

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