Benzylamine → Benzyl(2,2-difluoroethyl)amine

HRID 2098412Notes

Reaction equation

HRID 2098412 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>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 7504BenzylamineHCID 8471TriethylamineHCID 2736499Chlorodifluoroethane (mixed isomers)

Product 1

HCID 50896648Benzyl(2,2-difluoroethyl)amineYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 20 g of water in an autoclave at an internal temperature of 120° C. for 6 hours. The two-phase solution is twice extracted with 50 ml of dichloromethane each time and the combined organic phases are washed with 50 ml of water and subsequently distilled. An amount of 5.2 g of N-benzyl-2,2-difluoroethanamine is obtained, which corresponds to a yield of 66%, based on benzylamine.

Workup

  1. extractionThe two-phase solution is twice extracted with 50 ml of dichloromethane each time
  2. washthe combined organic phases are washed with 50 ml of water
  3. distillationsubsequently distilled

Sources & evidence

ORD record
ord-cb10cf0ca6834f6592604232eca3bfec
Source dataset
uspto-grants-2013_05
Patent number
US08450528B2

Reaction notes

Loading…