Water → N-(2,4-difluorophenylmethyl)-N-[dimethyl(methoxymethyl)methyl]amine

HRID 636734Notes

Reaction equation

HRID 636734 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[CH:4]=[N:5][C:6]([CH3:11])([CH3:10])[CH2:7][O:8][CH3:9].[BH4-].[Na+].C([O-])(O)=O.[Na+].O>CO>[F:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6]([CH3:11])([CH3:10])[CH2:7][O:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 21255697N-(2,4-difluorobenzylidene)-N-[dimethyl(methoxymethyl)methyl]amine

Product 1

HCID 21255704N-(2,4-difluorophenylmethyl)-N-[dimethyl(methoxymethyl)methyl]amineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the obtained N-(2,4-difluorobenzylidene)-N-[dimethyl(methoxymethyl)methyl]amine in methanol (7 ml) was cooled to 0° C. in ice-water bath. To the solution was added NaBH4 (117.1 mg, 3.09 mmol). The mixture was gradually warmed to room temperature and stirred for 14 hours. The mixture was added to sat. NaHCO3 aqueous solution and water was added to dissolve the precipitated white solid. The mixture was then extracted three times with ethyl acetate and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ethyl acetate/triethylamine=50/25/1) to give N-(2,4-difluorophenylmethyl) -N-[dimethyl(methoxymethyl)methyl]amine (378.8 mg; 95% in 3 steps).

Workup

  1. additionwas added
  2. dissolutionto dissolve the precipitated white solid
  3. extractionThe mixture was then extracted three times with ethyl acetate
  4. dry with materialdried over MgSO4
  5. concentrationThe mixture was concentrated
  6. custompurified by silica gel chromatography (hexane/ethyl acetate/triethylamine=50/25/1)

Sources & evidence

ORD record
ord-a402ec5a46b14d0c874b28d64f926492
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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