Methylamine → 3-(Methylaminomethyl)pyridine

HRID 249468Notes

Reaction equation

HRID 249468 reaction equation
[OH-].[Na+].[CH3:3][NH2:4].Cl.[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12]Cl)[CH:7]=1>>[CH3:3][NH:4][CH2:12][C:8]1[CH:7]=[N:6][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 233943-(Chloromethyl)pyridine hydrochloride

Product 1

HCID 883933-(Methylaminomethyl)pyridineYield 42.6%

Procedure

To 25 ml of a 20% aqueous solution of NaOH stirred under cooling with ice-water, a 40% aqueous solution of methylamine (13.6 g, 0.175 mole) was added dropwise over 5 minutes, followed by further dropwise addition of an aqueous solution (10 ml) of 8.2 g (0.05 mole) of 3-pyridylmethyl chloride hydrochloride over 10 minutes. The mixture was further stirred at room temperature for 2 hours and, then, extracted with CH2Cl2 (100 ml×3). The extract was dried over MgSO4 and distilled to remove the solvent. The residue was subjected to vacuum distillation to give 2.6 g of the title compound as a yellow oil.

Workup

  1. extractionextracted with CH2Cl2 (100 ml×3)
  2. dry with materialThe extract was dried over MgSO4
  3. distillationdistilled
  4. customto remove the solvent
  5. distillationThe residue was subjected to vacuum distillation

Sources & evidence

ORD record
ord-336a9c1012f04346b4f49628f757fe09
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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