4-Methoxybenzylamine → 2,2-difluoro-N-(4-methoxybenzyl)ethanamine

HRID 2098417Notes

Reaction equation

HRID 2098417 reaction equation
[F:1][CH:2]([F:5])[CH2:3]Cl.[CH3:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=1>O>[F:1][CH:2]([F:5])[CH2:3][NH:13][CH2:12][C:11]1[CH:14]=[CH:15][C:8]([O:7][CH3:6])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 754524-Methoxybenzylamine2×HCID 2736499Chlorodifluoroethane (mixed isomers)

Product 1

HCID 609231912,2-difluoro-N-(4-methoxybenzyl)ethanamineYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An amount of 23.15 g (214 mmol) of 2,2-difluoro-1-chloroethane and 10 g (71 mmol) of 4-methoxybenzylamine 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-methoxybenzylamine hydrochloride present in the aqueous phase can be converted back into free 4-methoxybenzylamine by addition of sodium hydroxide solution. After distillation, 4.93 g of 2,2-difluoro-N-(4-methoxybenzyl)ethanamine are obtained, which corresponds to a yield of 68%, based on reacted 4-methoxybenzylamine.

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. additionHere also, the 4-methoxybenzylamine hydrochloride present in the aqueous phase can be converted back into free 4-methoxybenzylamine by addition of sodium hydroxide solution
  5. distillationAfter distillation, 4.93 g of 2,2-difluoro-N-(4-methoxybenzyl)ethanamine
  6. customare obtained

Sources & evidence

ORD record
ord-085a0b60b7cf43a18b57752ccae5b6c5
Source dataset
uspto-grants-2013_05
Patent number
US08450528B2

Reaction notes

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