4-Dimethylaminomethylbenzylamine → HCID 178470187, compound

HRID 1595379Notes

Reaction equation

HRID 1595379 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1)[CH3:3].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[C:21](=[N:27]O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=1>N1C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[NH:12][C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][N:2]([CH3:3])[CH3:1])=[CH:6][CH:7]=3)=[N:27][C:21]=2[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 1937144-DimethylaminomethylbenzylamineHCID 178472894HCID 178472894, compound

Product 1

HCID 178470187HCID 178470187, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(Dimethylaminomethyl)phenylmethylamine (11.7 g) and ethyl 3-(4-chlorophenyl)-2-hydroxyimino-3-oxopropionate (15.1 g) were dissolved in pyridine (220 ml) and the solution was refluxed under heating for 12 hr. The solvent was concentrated under reduced pressure and the obtained residue was subjected to silica gel column chromatography to give the objective ethyl 5-(4-chlorophenyl)-2-[4-(dimethylaminomethyl)phenyl]imidazole-4-carboxylate (9.0 g), melting point 175-176° C.

Workup

  1. temperaturethe solution was refluxed
  2. temperatureunder heating for 12 hr
  3. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8990023815794cd68951d6363c30363a
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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