Methylamine → 6-Bromo-N-methyl-3-pyridinemethanamine

HRID 1585019Notes

Reaction equation

HRID 1585019 reaction equation
[CH3:1][NH2:2].[Br:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][CH:5]=1>CC#N>[Br:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][NH:2][CH3:1])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 64246602-Bromo-5-bromomethylpyridine

Product 1

HCID 224503166-Bromo-N-methyl-3-pyridinemethanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 12.3 g of 40% aqueous methylamine solution and 40 ml of CH3CN was added 8.0 g of crude (6-bromo-3-pyridyl)methyl bromide with stirring. The mixture was further stirred at room temperature for 30 minutes. The reaction mixture thus obtained was concentrated and the residue was diluted with toluene and subjected to azeotropic distillation to remove the water. Then, the soluble fraction was extracted with Et2O. The Et2O layer was dried over MgSO4 and concentrated to recover 4.4 g of the title compound as a yellow oil.

Workup

  1. stirringThe mixture was further stirred at room temperature for 30 minutes
  2. customThe reaction mixture thus obtained
  3. concentrationwas concentrated
  4. additionthe residue was diluted with toluene
  5. distillationsubjected to azeotropic distillation
  6. customto remove the water
  7. extractionThen, the soluble fraction was extracted with Et2O
  8. dry with materialThe Et2O layer was dried over MgSO4
  9. concentrationconcentrated
  10. customto recover 4.4 g of the title compound as a yellow oil

Sources & evidence

ORD record
ord-49a6bad4c2834486aa530dd34ef9332e
Source dataset
uspto-grants-1999_08
Patent number
US05935981

Reaction notes

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