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

HRID 131260Notes

Reaction equation

HRID 131260 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].O>CN(C)C=O>[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

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-bromomethylbenzoate (22.8 g) in N,N-dimethylformamide (450 ml) is added dropwise 50% aqueous dimethylamine solution (27 mL) and the mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into water with ice and extracted with ethyl acetate. The extract is washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resultant crude product is purified by flash column chromatography on silica gel (Solvent; chloroform:methanol=10:1) to give methyl 4-[(dimethylamino) methyl]benzoate (27.5 g, yield; 99%) as brown oil. MS (APCI) m/z: 194 [M+H]+

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant crude product is purified by flash column chromatography on silica gel (Solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-db3a7e69273649aeb38cdca4dc47a564
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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