Dimethylamine, hydrochloride → N-(4-dimethylaminomethylphenylmethyl)acetamide

HRID 1595377Notes

Reaction equation

HRID 1595377 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.Cl.[CH3:15][NH:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:15][N:16]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1)[CH3:17]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 15550682N-((4-(chloromethyl)phenyl)methyl)acetamide

Product 1

HCID 21703715N-(4-dimethylaminomethylphenylmethyl)acetamideYield 136.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(4-Chloromethylphenylmethyl)acetamide (20.0 g) and dimethylamine hydrochloride (9.1 g) were dissolved in acetonitrile (190 ml), and potassium carbonate (28 g) was added. The mixture was refluxed under heating overnight. An insoluble solid was filtered off and the solvent was evaporated to give the objective N-(4-dimethylaminomethylphenylmethyl)acetamide (28.4 g) as an oil.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating overnight
  3. filtrationAn insoluble solid was filtered off
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-003b84edd6804181a283ab5e3d577154
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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