Dimethylamine → N-dimethylaminoacetyl-N-(3-dimethylamino-4-methoxymethoxybenzyl)aniline

HRID 1032951Notes

Reaction equation

HRID 1032951 reaction equation
Cl[CH2:2][C:3]([N:5]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([N:23]([CH3:25])[CH3:24])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:26][NH:27][CH3:28]>>[CH3:26][N:27]([CH2:2][C:3]([N:5]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([N:23]([CH3:25])[CH3:24])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4])[CH3:28]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 19026964N-chloroacetyl-N-(3-dimethylamino-4-methoxymethoxybenzyl)aniline

Product 1

HCID 54526197N-dimethylaminoacetyl-N-(3-dimethylamino-4-methoxymethoxybenzyl)aniline

Procedure

To the compound (2) (1.68 g, 4.63 mmol) obtained above was added a 50% aqueous solution of dimethylamine (8 ml) under ice-cooling. After being stirred at room temperature for 1.5 hours, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel to give the object compound (3). Yield 1.57 g (91%).

Workup

  1. temperaturecooling
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0421450dde974a42b9d248567145a723
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

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