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

HRID 2270468Notes

Reaction equation

HRID 2270468 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-2d88314a96094902b80f5a858c2080e6
Source dataset
uspto-grants-2001_12
Patent number
US06331542B1

Reaction notes

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