Methylamine → N-(2-Methoxyphenyl)-4-(methylamino)methylbenzamide

HRID 2455

Reaction equation

HRID 2455 reaction equation
Cl[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[O:8])=[CH:5][CH:4]=1.[CH3:20][NH2:21]>O1CCOCC1>[CH3:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:7](=[O:8])[C:6]1[CH:18]=[CH:19][C:3]([CH2:2][NH:21][CH3:20])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 196899684-Chloromethyl-N-(2-methoxyphenyl)benzamide

Product 1

HCID 19690083N-(2-Methoxyphenyl)-4-(methylamino)methylbenzamideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4-Chloromethyl-N-(2-methoxyphenyl)benzamide (400 mg, 1.45 mmol) was dissolved in dioxane (4 ml) and then mixed with 50% methylamine aqueous solution (4 ml) at room temperature. After 1 hour of stirring at the same temperature, dioxane was removed by evaporation, and the resulting residue was diluted with methylene chloride (10 ml). After drying on anhydrous sodium carbonate, the solvent was removed by evaporation to obtain 500 mg (100%) of the title compound in the form of colorless oil.

Workup

  1. customwas removed by evaporation
  2. additionthe resulting residue was diluted with methylene chloride (10 ml)
  3. dry with materialAfter drying on anhydrous sodium carbonate
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-1e483b3adf244fe28b89df6ce80d81bc
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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