Dimethylamine → Methyl 4-(Dimethylamino)methyl-3-methoxybenzoate

HRID 1958809Notes

Reaction equation

HRID 1958809 reaction equation
[CH3:1][NH:2][CH3:3].Br[CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[O:16][CH3:17]>C(O)C.C1COCC1.O.C([O-])([O-])=O.[Na+].[Na+]>[CH3:1][N:2]([CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[O:16][CH3:17])[CH3:3]

Participants

7

Reactant 2

HCID 674DimethylamineHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoate

Product 1

HCID 21182956Methyl 4-(Dimethylamino)methyl-3-methoxybenzoate

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a solution of dimethyl amine (0.9 mL of a 5.6 M solution in ethanol) in THF (20 mL), a solution of methyl 4-(bromomethyl)-3-methoxybenzoate (500 mg, 2.06 mmol) was added. The mixture was stirred at rt for 35 min before it was diluted with water (150 mL) and sat. aq. Na2CO3-solution (50 mL) and extracted with EA (70 mL). The org. extract was separated, dried over Na2SO4, filtered, evaporated and dried to give methyl 4-dimethylaminomethyl-3-methoxy-benzoate as a colourless oil (420 mg). LC-MS: tR=0.61 min, [M+1]+=224.04.

Workup

  1. extractionextracted with EA (70 mL)
  2. extractionextract
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried

Sources & evidence

ORD record
ord-b1fe79b1de2c47a7ba4290b41e80169d
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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