4-Chlorobenzylamine → HCID 60921631, compound

HRID 2098416Notes

Reaction equation

HRID 2098416 reaction equation
[F:1][CH:2]([F:5])[CH2:3]Cl.[Cl:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=1>O>[F:1][CH:2]([F:5])[CH2:3][NH:12][CH2:11][C:10]1[CH:13]=[CH:14][C:7]([Cl:6])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 660364-Chlorobenzylamine2×HCID 2736499Chlorodifluoroethane (mixed isomers)

Product 1

HCID 60921631HCID 60921631, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An amount of 22.4 g (207 mmol) of 2,2-difluoro-1-chloroethane and 10 g (69 mmol) of 4-chlorobenzylamine are heated in an autoclave at an internal temperature of 120° C. for 16 hours. Subsequently, 50 g of water are added and the aqueous phase is separated. The aqueous phase is again extracted with 2,2-difluoro-1-chloroethane and the combined organic phases are distilled as described in Example 1.1. Here also, the 4-chlorobenzylamine hydrochloride which is present in the aqueous phase can be converted back into free 4-chlorobenzylamine by addition of sodium hydroxide solution. After distillation, 4.25 g of 2,2-difluoro-N-(4-chlorobenzyl)ethanamine are obtained, which corresponds to a yield of 61%, based on reacted 4-chlorobenzylamine

Workup

  1. customthe aqueous phase is separated
  2. extractionThe aqueous phase is again extracted with 2,2-difluoro-1-chloroethane
  3. distillationthe combined organic phases are distilled
  4. additioncan be converted back into free 4-chlorobenzylamine by addition of sodium hydroxide solution
  5. distillationAfter distillation, 4.25 g of 2,2-difluoro-N-(4-chlorobenzyl)ethanamine
  6. customare obtained

Sources & evidence

ORD record
ord-9f8ebe837b5540ca87e972b94cc3ce0f
Source dataset
uspto-grants-2013_05
Patent number
US08450528B2

Reaction notes

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