Dimethylamine → Methyl 4-((dimethylamino)methyl)benzoate

HRID 610413Notes

Reaction equation

HRID 610413 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[CH3:13][NH:14][CH3:15]>CO>[CH3:13][N:14]([CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[CH3:15]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 12361573Methyl 4-((dimethylamino)methyl)benzoateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(bromomethyl)benzoate (2.0 g, 8.73 mmol) was added to a saturated solution of dimethylamine in methanol. After stirring for 25 min, the solution was concentrated and the residue was partitioned between 1N NaOH and ethyl acetate. The organic layer was washed with saturated brine, dried (MgSO4), filtered, and concentrated to provide the title compound as a colorless liquid (1.67 g, 99%). 1H NMR (250 MHz, CDCl3) δ 8.00 (d, 2H), 7.39 (d, 2H), 3.91 (s, 3H), 3.47 (d, 2H), 2.25 (s, 6H).

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue was partitioned between 1N NaOH and ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31df0852d3c844bb8a22fc415f184a2e
Source dataset
uspto-grants-1999_12
Patent number
US05998470

Reaction notes

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