Cysteamine Hydrochloride → 2-{[(Pyridin-3-yl)methyl]sulfanyl}ethan-1-amine

HRID 1583408Notes

Reaction equation

HRID 1583408 reaction equation
[OH-].[Na+].Cl.Cl[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.Cl.[SH:13][CH2:14][CH2:15][NH2:16]>C(O)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][S:13][CH2:14][CH2:15][NH2:16])[CH:7]=1

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 233943-(Chloromethyl)pyridine hydrochloride

Product 1

HCID 134987022-{[(Pyridin-3-yl)methyl]sulfanyl}ethan-1-amineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

16.8 g of sodium hydroxide was dissolved in 350 ml of ethanol and 17.2 g of 3-chloromethylpyridine hydrochloride and 23.7 g of 2-mercaptoethanamine hydrochloride were added with ice bath cooling. The reaction mixture was allowed to warm to room temperature over 2 hours, was concentrated, diluted with water, and extracted with 3×100 ml of dichloromethane. The combined organic layers were washed with saturated brine, dried over potassium carbonate and concentrated. The residue was distilled to give 12.30 g (70%) of 2-[[(3-pyridyl)methyl]thio]ethanamine, bp 115°-125° C./0.1 mm.

Workup

  1. temperaturecooling
  2. concentrationwas concentrated
  3. additiondiluted with water
  4. extractionextracted with 3×100 ml of dichloromethane
  5. washThe combined organic layers were washed with saturated brine
  6. dry with materialdried over potassium carbonate
  7. concentrationconcentrated
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-666bb7d55530477185b67764c524726a
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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