Cysteamine Hydrochloride → 2-{[(Pyridin-4-yl)methyl]sulfanyl}ethan-1-amine

HRID 745519Notes

Reaction equation

HRID 745519 reaction equation
[OH-].[Na+].Cl.[SH:4][CH2:5][CH2:6][NH2:7].Cl.N1C=CC=CC=1.Cl[CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1>C(O)C>[N:20]1[CH:21]=[CH:22][C:17]([CH2:16][S:4][CH2:5][CH2:6][NH2:7])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 23313627HCID 23313627, compound

Product 1

HCID 134987042-{[(Pyridin-4-yl)methyl]sulfanyl}ethan-1-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

34.1 g of sodium hydroxide was dissolved in 500 ml of ethanol under an argon atmosphere and 48.6 g of 2-mercaptoethanamine hydrochloride and 35 g of 4-chloromethylpyridine pyridine hydrochloride were added with ice bath cooling. The reaction mixture was allowed to warm to room temperature over 2 hours, was concentrated, diluted with 300 ml of water and was extracted with 3×150 ml of dichloromethane. The combined organic layers were washed with 100 ml of saturated brine, dried over potassium carbonate and were evaporated to a dark oil which was distilled. The fractions bp 120°-130° C./0.1 mm amounted to 30.68 g (85%) of 2-[[(4-pyridyl)methyl]thio]ethanamine.

Workup

  1. temperaturecooling
  2. concentrationwas concentrated
  3. additiondiluted with 300 ml of water
  4. extractionwas extracted with 3×150 ml of dichloromethane
  5. washThe combined organic layers were washed with 100 ml of saturated brine
  6. dry with materialdried over potassium carbonate
  7. customwere evaporated to a dark oil which
  8. distillationwas distilled

Sources & evidence

ORD record
ord-0535977a567d475a8169cd00ba652490
Source dataset
uspto-grants-1986_07
Patent number
US04599336

Reaction notes

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