Dimethylamine → N,N-Dimethyl-4-nitrobenzylamine

HRID 450067Notes

Reaction equation

HRID 450067 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH3:18][NH:19][CH3:20]>C(#N)C>[CH3:18][N:19]([CH3:20])[CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 278498N,N-Dimethyl-4-nitrobenzylamineYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-nitrobenzyl bromide (4 g, 18.5 mmol) and potassium carbonate (7.65 g, 55.5 mmol) in acetonitrile (50 ml) at 0-5° C. was added 40% aqueous dimethyl amine solution (1.5 eq). After 1 hr at room temperature, the solvent was evaporated; the crude material was dissolved in water and extracted with ethyl acetate. The organic layer was dried and concentrated to give dimethyl-(4-nitro-benzyl)-amine (2.8 g, 84%)

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe crude material was dissolved in water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bd2fb2eba8554bfdb8b410859dc681eb
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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