Potassium Iodide → HCID 18789916, compound

HRID 1106875Notes

Reaction equation

HRID 1106875 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:6]=1[O:7][CH2:8][CH2:9]Br)(=[O:3])[CH3:2].[I-].[K+].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][NH:32][CH3:33])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>CN(C)C=O>[C:1]([NH:4][C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:6]=1[O:7][CH2:8][CH2:9][N:32]([CH2:31][CH2:30][C:24]1[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=1)[CH3:33])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 77039N-MethylhomoveratrylamineHCID 18789971HCID 18789971, compound

Product 1

HCID 18789916HCID 18789916, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A portion (440 mg, 1.46 mmol) of the 1-(2-acetamido-4-nitrophenoxy)-2-bromoethane produced in (2) above was dissolved in dimethylformamide (5 ml) and, thereafter, potassium iodide (267 mg, 1.608 mmol) and 2-(3,4-dimethoxyphenyl)-N-methylethylamine (0.81 ml, 4.36 mmol) were added to the solution, which was stirred at 70° C. for 1.5 h. Thereafter, the solvent was evaporated from the reaction mixture and the residue was subjected to extraction with ethyl acetate. The organic layer was washed with water four times and dried with sodium sulfate, followed by evaporation of the solvent, with the resulting residue being purified by being subjected to column chromatography on silica gel using, as an eluent, chloroform containing methanol (6%) to yield the end compound 1-(2-acetamido-4-nitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (590 ml) as a yellow caramel-like substance.

Workup

  1. customThereafter, the solvent was evaporated from the reaction mixture
  2. extractionthe residue was subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with water four times
  4. dry with materialdried with sodium sulfate
  5. customfollowed by evaporation of the solvent, with the resulting residue being
  6. custompurified
  7. additionchloroform containing methanol (6%)

Sources & evidence

ORD record
ord-c82e879deb034f8db8a8085c09799b08
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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