Dimethylamine → 4,5-difluoro-2-hydroxy-n,n-dimethylbenzylamine

HRID 1071213Notes

Reaction equation

HRID 1071213 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:10]=O.O.[CH3:13][NH:14][CH3:15]>>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:13][N:14]([CH3:10])[CH3:15])=[C:4]([OH:9])[CH:3]=1

Participants

5

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 962WaterHCID 759273,4-Difluorophenol

Product 1

HCID 102415484,5-difluoro-2-hydroxy-n,n-dimethylbenzylamine

Conditions

Temperature
0 °C

Procedure

400 g of 3,4-difluorophenol are initially charged in 408 ml of 40% aqueous dimethylamine solution and cooled to 0° C. At 0-5° C., 276 ml of 37% aqueous formaldehyde solution are added dropwise within 60 min. The mixture is kept at 5-10° C. for 2 hours and subsequently stirred at room temperature for 20 hours. The mixture is admixed with 600 ml of water. The organic phase is removed, the aqueous phase is extracted twice with dichloromethane, the combined organic phases are dried and the solvent is distilled off under reduced pressure. The crude product is subsequently fractionally distilled under reduced pressure. 395 g (65% of theory) of a colourless liquid having a boiling point of 93° C. at 16 mbar are obtained.

Workup

  1. customThe organic phase is removed
  2. extractionthe aqueous phase is extracted twice with dichloromethane
  3. customthe combined organic phases are dried
  4. distillationthe solvent is distilled off under reduced pressure
  5. distillationThe crude product is subsequently fractionally distilled under reduced pressure
  6. customare obtained

Sources & evidence

ORD record
ord-c776fe56048145a288fc5c2652a86070
Source dataset
uspto-grants-2005_06
Patent number
US06903239B2

Reaction notes

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