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

HRID 2098407Notes

Reaction equation

HRID 2098407 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.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

5

Reactant 3

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

Product 1

HCID 50896648Benzyl(2,2-difluoroethyl)amineYield 70.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

An amount of 2 g (20 mmol) of 2,2-difluoro-1-chloroethane and 4.5 g (41 mmol) of benzylamine are heated in 62 g of N-methylpyrrolidone in an autoclave at an internal temperature of 120° C. for 16 hours. Subsequently, 50 g of 1N hydrochloric acid are added and the solvent is removed under vacuum. The residue is taken up in 50 ml of water and 50 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 2.4 g of N-benzyl-2,2-difluoroethanamine is obtained, which corresponds to a yield of 66.2%, based on 2,2-difluoro-1-chloroethane used.

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-4557f4def249429b8ad9cf0919123195
Source dataset
uspto-grants-2013_05
Patent number
US08450528B2

Reaction notes

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