Ethanol → 6-Chloro-N-methyl-3-pyridinemethanamine

HRID 483350Notes

Reaction equation

HRID 483350 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[CH3:10][NH2:11].C(O)C>O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][NH:11][CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 110948836-Chloro-N-methyl-3-pyridinemethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of the product of Example 4(b), 2-chloro-5-chloromethylpyridine, (8.1 g, 0.05 mol), methylamine (60 ml of a 30% w/v solution in water, 0.5 mol) and ethanol (100 ml) was heated, with stirring, under reflux for 5 hours. The reaction mixture was then cooled to ambient temperature (20° C.) and the solvent removed by evaporation under reduced pressure to give a brown oil. The product, N-(6-chloro-3-pyridylmethyl)-N-methylamine, was isolated from this oil by flash chromatography using silica gel, 230 to 400 US mesh (0.062 mm to 0.037 mm), with 10% v/v methanol/dichloromethane as eluent, as a brown oil (5.96 g, 76.1%).

Workup

  1. temperatureunder reflux for 5 hours
  2. customthe solvent removed by evaporation under reduced pressure
  3. customto give a brown oil

Sources & evidence

ORD record
ord-b61a381a138640da9851f75748ca0457
Source dataset
uspto-grants-1993_07
Patent number
US05225423

Reaction notes

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