Methylamine → 3-(Methylaminomethyl)pyridine

HRID 1954936Notes

Reaction equation

HRID 1954936 reaction equation
[CH3:1][NH2:2].Cl.[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Cl)[CH:5]=1>>[CH3:1][NH:2][CH2:10][C:6]1[CH:5]=[N:4][CH:9]=[CH:8][CH:7]=1

Participants

3

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-f894e230c1964029b7aa138c9b546fae
Source dataset
uspto-grants-2000_09
Patent number
US06124297

Reaction notes

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