[4-(Morpholin-4-ylmethyl)phenyl]methanamine → Ethyl 5-(4-chlorophenyl)-2-[4-(morpholinomethyl)phenyl]imidazole-4-carboxylate

HRID 1595376Notes

Reaction equation

HRID 1595376 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH2:15])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=O)[C:24](=[N:30]O)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=1>N1C=CC=CC=1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[NH:15][C:14]([C:11]3[CH:10]=[CH:9][C:8]([CH2:7][N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)=[CH:13][CH:12]=3)=[N:30][C:24]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 2795501[4-(Morpholin-4-ylmethyl)phenyl]methanamineHCID 178472894HCID 178472894, compound

Product 1

HCID 178470186Ethyl 5-(4-chlorophenyl)-2-[4-(morpholinomethyl)phenyl]imidazole-4-carboxylateYield 61.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(Morpholinomethyl)phenylmethylamine (8 g) and ethyl 3-(4-chlorophenyl) -2-hydroxyimino-3-oxopropionate (8.26 g) were dissolved in pyridine (120 ml) and the mixture was refluxed under heating for 12 hr. The solvent was evaporated under reduced pressure and the obtained residue was subjected to silica gel column chromatography to give the objective ethyl 5-(4-chlorophenyl)-2-[4-(morpholinomethyl)phenyl]imidazole-4-carboxylate (8.46 g), melting point 183-185° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 12 hr
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d44807d35368431c8724c55ddde81c27
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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