Methylamine → N,N-dimethyl-6-(methylamino)-2-Pyridinemethanamine

HRID 1154695Notes

Reaction equation

HRID 1154695 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]([CH3:11])[CH3:10])[N:3]=1.[CH3:12][NH2:13]>C(O)C>[CH3:10][N:9]([CH2:8][C:4]1[N:3]=[C:2]([NH:13][CH3:12])[CH:7]=[CH:6][CH:5]=1)[CH3:11]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 20434272[(6-Chloropyridin-2-yl)methyl]dimethylamine

Product 1

HCID 20434276N,N-dimethyl-6-(methylamino)-2-Pyridinemethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-6-dimethylaminomethylpyridine (6.8 g, 0.04 mol), methylamine (12.0 g, 0.32 mole) and ethanol (25 ml) are heated at 180°-200° C. for 36 hours in a sealed reaction vessel. The solvent is removed in vacuo and the residue is made basic with excess sodium hydroxide and extracted with ether. The ether extract is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. This gives 5.8 g of amber oil. The oil is distilled at 90°-100° C. at 1.8 mm and is further purified by chromatography. This gives 2.7 g of 6-dimethylaminomethyl-2-methylaminopyridine as a colorless oil.

Workup

  1. customThe solvent is removed in vacuo
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. dry with materialis dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. distillationThe oil is distilled at 90°-100° C. at 1.8 mm
  8. customis further purified by chromatography

Sources & evidence

ORD record
ord-89d8e7b7e5cd4684ada868c0ef08d323
Source dataset
uspto-grants-1984_12
Patent number
US04490533

Reaction notes

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