Cysteamine Hydrochloride → 2-(6-Dimethylaminomethyl-2-pyridylthio)ethylamine

HRID 1154701Notes

Reaction equation

HRID 1154701 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[H-].[Na+].[CH3:8][N:9]([CH2:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[CH:14][CH:13]=1)[CH3:10]>CN(C)C=O.C(O)C>[CH3:8][N:9]([CH2:11][C:12]1[N:17]=[C:16]([S:5][CH2:4][CH2:3][NH2:2])[CH:15]=[CH:14][CH:13]=1)[CH3:10]

Participants

6

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 24758Sodium hydrideHCID 20434272[(6-Chloropyridin-2-yl)methyl]dimethylamine

Product 1

HCID 133648672-(6-Dimethylaminomethyl-2-pyridylthio)ethylamineYield 44.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

Cysteamine hydrochloride (3.43 g, 0.030 mol) is added to a suspension of 60% sodium hydride in mineral oil (2.5 g, 0.0625 mol) in dry dimethylformamide (30 ml) and is warmed to 80° C. A solution of 6-dimethylaminomethyl-2-chloropyridine (5.0 g, 029.4 mol) in 30 ml of dry dimethylformamide is added dropwise and the reaction temperature is increased to 125° C. for 2 hours. The reaction is cooled, diluted with ethanol (60 ml) and the salts are removed by filtration before evaporating to dryness. This residue is dissolved in chloroform, washed with water and extracted into dilute hydrochloric acid. The acidic extract is neutralized with sodium carbonate and the product is extracted into chloroform, dried and evaporated to give 4.4 g. This residual oil is distilled to give 2.74 g of pure product, bp: 109°-114° C./0.25 mm.

Workup

  1. temperaturethe reaction temperature is increased to 125° C. for 2 hours
  2. temperatureThe reaction is cooled
  3. customthe salts are removed by filtration
  4. custombefore evaporating to dryness
  5. dissolutionThis residue is dissolved in chloroform
  6. washwashed with water
  7. extractionextracted into dilute hydrochloric acid
  8. extractionThe acidic extract
  9. extractionthe product is extracted into chloroform
  10. customdried
  11. customevaporated
  12. customto give 4.4 g
  13. distillationThis residual oil is distilled

Sources & evidence

ORD record
ord-3d75b362af3f489488cb2689aac3898a
Source dataset
uspto-grants-1984_12
Patent number
US04490533

Reaction notes

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