Methylamine → N,2-Dimethyl-4-pyridinemethanamine

HRID 1078019Notes

Reaction equation

HRID 1078019 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][N:3]=1.[CH3:10][NH2:11]>Br>[CH3:10][NH:11][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 9942144(2-Methylpyridin-4-yl)methanol

Product 1

HCID 10374514N,2-Dimethyl-4-pyridinemethanamineYield 68%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A stirred solution of 0.86 g (6.98 mmol) of 2-methyl-4-hydroxymethylpyridine (R. B. Katz et al., Synthetic Communications, 19, 1989, 317-325) in 48% aqueous HBr was heated at reflux for four days. The reaction mixture was cooled and added dropwise to 20 ml of 40% aqueous methylamine. The volatiles were removed under reduced pressure, and the residue was slurried in CH2Cl2 and then filtered. The filter cake was washed with CH2Cl2, EtOAc, CH3CN, and 10% MeOH in CH3CN. The filtrate was concentrated, and the residue was flash chromatographed on silica, eluting CH2Cl2 :NH3-saturated MeOH (9:1). Consequently, 0.65 g (68% yield) of methyl-(2-methyl-pyridin-4-ylmethyl)-amine (39) was obtained as a colorless liquid.

Workup

  1. temperatureat reflux for four days
  2. temperatureThe reaction mixture was cooled
  3. customThe volatiles were removed under reduced pressure
  4. filtrationfiltered
  5. washThe filter cake was washed with CH2Cl2, EtOAc, CH3CN, and 10% MeOH in CH3CN
  6. concentrationThe filtrate was concentrated
  7. customchromatographed on silica
  8. washeluting CH2Cl2

Sources & evidence

ORD record
ord-28ebce91a627498c9d38373852765767
Source dataset
uspto-grants-1996_08
Patent number
US05545744

Reaction notes

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