N,N-Dimethyl-1,3-propanediamine → N1,N1-Dimethyl-N3-(4-nitrophenyl)-1,3-propanediamine

HRID 1357552Notes

Reaction equation

HRID 1357552 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].C(=O)([O-])[O-].[K+].[K+].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][NH:6][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[CH3:7]

Participants

4

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 15868541N1,N1-Dimethyl-N3-(4-nitrophenyl)-1,3-propanediamineYield 109.7%

Conditions

Temperature
70 °C

Procedure

N,N-Dimethylpropane-1,3-diamine (4.90 ml, 39 mmol) and potassium carbonate (6.37 g, 46 mmol) were added to 1-fluoro-4-nitrobenzene (5.0 g, 35 mmol) and the mixture was heated at 70° C. for 3 hours. Insoluble material was removed by filtration and the filtrate was concentrated. The residue was dissolved in ethyl acetate (100 ml) and the solution was washed with water (3×100 ml) and saturated sodium chloride (100 ml) and dried. The solvent was removed by evaporation to give the product as a yellow oil (8.57 g). MS (MH+): 248.

Workup

  1. customInsoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  4. washthe solution was washed with water (3×100 ml) and saturated sodium chloride (100 ml)
  5. customdried
  6. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-ff8696eab98c42739ff2a002fdf194e5
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

Loading…