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

HRID 1356502Notes

Reaction equation

HRID 1356502 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, dired (MgSO4), filtered, and concentrated to provide the title compound as a colorless liquid (1.67 g, 99%). 1H NMR (250 MHz, CDCl3) δ8.00 (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, dired (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a3f90001046f4428b4651a255fd0cdab
Source dataset
uspto-grants-2003_07
Patent number
US06586466B2

Reaction notes

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