Triethylamine → HCID 20222380, compound

HRID 980222Notes

Reaction equation

HRID 980222 reaction equation
[NH2:1][CH:2]([CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.C(N(CC)CC)C.[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1>C(#N)C>[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH:1][CH:2]([CH2:9][O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[CH2:3][N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 201311651-[2-amino-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole

Product 1

HCID 20222380HCID 20222380, compoundYield 3.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-[2-amino-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole (1.70 g, 0.0065M) in dry acetonitrile (10 ml) containing triethylamine (0.5 ml) was treated with 4-methoxybenzyl chloride (1.12 g, 0.0072M) and heated under reflux for 18 hours under a stream of dry nitrogen. The solvent was evaporated off under reduced pressure and the residue was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and dried (MgSO4). The solvent was evaporated off under reduced pressure to give the crude product as an oil which was further purified by chromatography (silica gel), 10% ethanol in chloroform) to give N-[(4-methoxyphenyl)methyl]-α-[[(4-methoxyphenyl)methoxy]methyl]-1H-imidazole-1-ethanamine (0.09 g ) as a pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours under a stream of dry nitrogen
  3. customThe solvent was evaporated off under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated off under reduced pressure
  8. customto give the crude product as an oil which
  9. customwas further purified by chromatography (silica gel), 10% ethanol in chloroform)

Sources & evidence

ORD record
ord-770916f59a084b4f882ba95772c44e01
Source dataset
uspto-grants-1987_01
Patent number
US04636518

Reaction notes

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