Dimethylamine → Methyl 6-(dimethylamino)methylnicotinate

HRID 2356762Notes

Reaction equation

HRID 2356762 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1.[CH3:13][NH:14][CH3:15].O>O1CCCC1>[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][N:4]=1)[CH3:15]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 127522376-Bromomethyl-nicotinic acid methyl ester

Product 1

HCID 57573795Methyl 6-(dimethylamino)methylnicotinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-bromomethylnicotinate (350 mg) in tetrahydrofuran (5 ml) was added a 50% aqueous dimethylamine solution (3 ml), and the mixture was vigorously stirred at room temperature for 10 minutes. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=100:1) to obtain methyl 6-(dimethylamino)methylnicotinate (276 mg) as brownish powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-751d0a836afe4ac692c7510014370619
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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