Dimethylamine → N,N-dimethyl-1-(3-methyl-4-nitrophenyl)methanamine

HRID 402670Notes

Reaction equation

HRID 402670 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Br.[CH3:13][NH:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:13][N:14]([CH3:15])[CH2:5][C:4]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 44459783-Methyl-4-nitrobenzyl bromide

Product 1

HCID 53486119N,N-dimethyl-1-(3-methyl-4-nitrophenyl)methanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methyl-4-nitrobenzyl bromide (1.0 g, 4.3 mmol), anhydrous dimethylamine (0.34 mL, 5.1 mmol) and potassium carbonate (1.5 g, 0.011 mol) in N,N-dimethylformamide (4.5 mL) was stirred at 70° C. for 12 h. Cooled to ambient temperature, the reaction mixture was poured into ice water, extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated to afford N,N-dimethyl-1-(3-methyl-4-nitrophenyl)methanamine as oil (0.80 g, y. 95%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-24615e3b449d4f09b1ac4374387dbff1
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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