Potassium Iodide → HCID 28574847, compound

HRID 1754966Notes

Reaction equation

HRID 1754966 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]([CH3:7])[CH3:6].[I-].[K+].C(N(CC)CC)C.[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][C:19]=1[CH3:25]>C1(C)C=CC=CC=1.O>[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][CH2:3][CH2:4][N:5]([CH3:7])[CH3:6])=[CH:20][C:19]=1[CH3:25]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 233594-Bromo-3-methylanilineHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 28574847HCID 28574847, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

2-Chloro-N,N-dimethylethylamine hydrochloride (372 mg, 2.58 mmol), potassium iodide (428 mg, 2.58 mmol) and triethylamine (0.719 ml, 5.16 mmol) were added to a solution of 4-bromo-3-methylaniline (400 mg, 2.15 mmol) in toluene (5.0 ml), and the mixture was heated with stirring at 110° C. for 17 hours. The reaction mixture was cooled and water was then added, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and saturated brine and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-methanol) to give N′-(4-bromo-3-methyl-phenyl)-N,N-dimethyl-ethane-1,2-diamine (100 mg, 18%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was sequentially washed with water and saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-e8a6dde317d945a0b193e718c3d88cff
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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