Imidazole → HCID 57246391, compound

HRID 2393292Notes

Reaction equation

HRID 2393292 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O.[CH2:19]([NH:24][CH2:25][C:26]1[CH:31]=[C:30](Br)[CH:29]=[CH:28][C:27]=1[O:33][CH3:34])[CH2:20][CH2:21][CH2:22][CH3:23]>C(OCC)(=O)C>[CH2:19]([NH:24][CH2:25][C:26]1[CH:31]=[C:30]([C:2]2[NH:1][CH:5]=[CH:4][N:3]=2)[CH:29]=[CH:28][C:27]=1[O:33][CH3:34])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 4716710HCID 4716710, compound

Product 1

HCID 57246391HCID 57246391, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Imidazole (11.8 g, 0.173 mol), potassium carbonate (0.147 mol), cuprous chloride (1.4 g, 0.014 mol), and N-methylpyrrolidone (270 ml) were added to N-pentyl-(5-bromo-2-methoxyphenyl) methylamine (38.0 g, 0.133 mol), and then the mixture was heated with stirring at 178°-182° C. for 7 hours. The reaction mixture was cooled and added with ethyl acetate (200 ml), and then, inorganic salts and the like were removed by filtration and the solvent was evaporated. The residue was extracted with ethyl acetate, and the extract was washed with 10% aqueous ammonia and then with saturated brine. After dryness over anhydrous sodium sulfate, the solvent was evaporated. The residue was purified by silica gel chromatography (Wako Gell C-300: 360 g, eluent: methyl alcohol/ethyl acetate=1/10 to 1/3) to give N-pentyl-(5-imidazolyl-2-methoxyphenyl)methylamine (21.3 g) as oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled
  3. custominorganic salts and the like were removed by filtration
  4. customthe solvent was evaporated
  5. extractionThe residue was extracted with ethyl acetate
  6. washthe extract was washed with 10% aqueous ammonia
  7. customAfter dryness over anhydrous sodium sulfate, the solvent was evaporated
  8. customThe residue was purified by silica gel chromatography (Wako Gell C-300: 360 g, eluent: methyl alcohol/ethyl acetate=1/10 to 1/3)

Sources & evidence

ORD record
ord-62c30bfb4131445196e6437d4e8abc5c
Source dataset
uspto-grants-1998_09
Patent number
US05807860

Reaction notes

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