Methylamine → HCID 15477307, compound

HRID 249497Notes

Reaction equation

HRID 249497 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>>[CH3:1][NH:2][CH2:10][C:7]1[CH:8]=[N:9][C:4]([CH3:3])=[CH:5][CH:6]=1

Participants

3

Reactant 2

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

Product 1

HCID 15477307HCID 15477307, compound

Procedure

A mixture of 16.6 g of 40% aqueous MeNH2 solution and 52 ml of CH2CN 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-4eed027a914a467cabb9b25dc08bff11
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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