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

HRID 2098408Notes

Reaction equation

HRID 2098408 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>>[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 3

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

Product 1

HCID 50896648Benzyl(2,2-difluoroethyl)amineYield 41.1%

Procedure

An amount of 5 g (49.7 mmol) of 2,2-difluoro-1-chloroethane and 11.3 g (105 mmol) of benzylamine are heated in an autoclave at an internal temperature of 120° C. for 16 hours. Subsequently, 100 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 3.5 g of N-benzyl-2,2-difluoroethanamine is obtained, which corresponds to a yield of 41%, 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-4591e11a65fc46f39fbc29012ab2fec1
Source dataset
uspto-grants-2013_05
Patent number
US08450528B2

Reaction notes

Loading…