Dimethylamine → HCID 69020193, compound

HRID 1591621Notes

Reaction equation

HRID 1591621 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7](CBr)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][NH:13][CH3:14].CO.[C:17](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:12][N:13]([CH2:17][C:4]1([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][CH:7]=[CH:10][CH2:11]1)[CH3:14]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 887MethanolHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 69020193HCID 69020193, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-nitrobenzyl bromide (2.16 g, 10 mmol), a solution of dimethylamine in methanol (2 M, 50 ml, 100 mmol), N,N-dimethylformamide (20 ml), and potassium carbonate (2.07 g, 15 mmol) was stirred for 12 hours. The methanol was removed by concentrating under reduced pressure and the mixture was treated with ethyl acetate (200 ml). The mixture was washed with water (100 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield 4-(N,N-dimethylaminomethyl)-4-nitrobenzene (0.98 g, 72% yield).

Workup

  1. customThe methanol was removed
  2. concentrationby concentrating under reduced pressure
  3. additionthe mixture was treated with ethyl acetate (200 ml)
  4. washThe mixture was washed with water (100 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92372def25c64414927cdea7a2add497
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Reaction notes

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