Methylamine → 2-Methyl-5-[(methylamino)methyl]pyridine

HRID 1682211Notes

Reaction equation

HRID 1682211 reaction equation
[CH3:1][NH2:2].[CH3:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10]Cl)=[CH:6][CH:5]=1>CC#N>[CH3:1][NH:2][CH2:10][C:7]1[CH:8]=[N:9][C:4]([CH3:3])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 122143385-(Chloromethyl)-2-methylpyridine

Product 1

HCID 154773072-Methyl-5-[(methylamino)methyl]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 16.6 g of 40% aqueous MeNH2 solution and 52 ml of CH3CN was cooled with ice and 6.08 g (0.043 mole in terms of pure product) of crude (6-methyl-3-pyridyl)methyl chloride was added dropwise with constant stirring. After completion of dropwise addition, the mixture was stirred at room temperature for 1.5 hours, at the end of which time the solvent was distilled off. The solid residue was extracted with CH2Cl2 and the CH2Cl2 layer was dried over MgSO4. The CH2Cl2 was distilled off and the residue was diluted with 70 ml of Et2O and filtered to remove the insoluble matter. Finally the filtrate was concentrated to recover 4.60 g of the title compound as a crude oil.

Workup

  1. additionwas added dropwise with constant stirring
  2. additionAfter completion of dropwise addition
  3. distillationwas distilled off
  4. extractionThe solid residue was extracted with CH2Cl2
  5. dry with materialthe CH2Cl2 layer was dried over MgSO4
  6. distillationThe CH2Cl2 was distilled off
  7. additionthe residue was diluted with 70 ml of Et2O
  8. filtrationfiltered
  9. customto remove the insoluble matter
  10. concentrationFinally the filtrate was concentrated
  11. customto recover 4.60 g of the title compound as a crude oil

Sources & evidence

ORD record
ord-7f1db4418be5499f957dbd784480a2e9
Source dataset
uspto-grants-1992_12
Patent number
US05175301

Reaction notes

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