Methylamine → [(2,6-Dichloropyridin-3-yl)methyl](methyl)amine

HRID 249476

Reaction equation

HRID 249476 reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1[C:9]([CH2:10]Cl)=[CH:8][CH:7]=[C:6]([Cl:12])[N:5]=1>C(#N)C>[Cl:3][C:4]1[C:9]([CH2:10][NH:2][CH3:1])=[CH:8][CH:7]=[C:6]([Cl:12])[N:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 6451791Pyridine, 2,6-dichloro-3-(chloromethyl)-

Product 1

HCID 22450421[(2,6-Dichloropyridin-3-yl)methyl](methyl)amineYield 83.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

In 50 ml of acetonitrile was dissolved 7.8 g (0.1 mole) of 40% aqueous methylamine and with stirring and ice-cooling, a solution of 3.9 g (0.02 mole) of 2,6-dichloro-3-pyridylmethyl chloride in 10 ml of acetonitrile was added dropwise over 5 minutes. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours and, then, concentrated. The residue was extracted with ether (30 ml×3) and dried over MgSO4. Finally, the solvent was distilled off to give 3.2 g of the title compound as a pale yellow oil.

Workup

  1. temperatureice-cooling
  2. additionAfter completion of the dropwise addition
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. concentrationconcentrated
  5. extractionThe residue was extracted with ether (30 ml×3)
  6. dry with materialdried over MgSO4
  7. distillationFinally, the solvent was distilled off

Sources & evidence

ORD record
ord-ab6497bd9ace42d8ae0d80948a8c2c49
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Linked notes

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