Cysteamine Hydrochloride → 2-(2-Aminoethylthiomethyl)-3-ethoxypyridine

HRID 444485Notes

Reaction equation

HRID 444485 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[Na].Cl.Cl[CH2:9][C:10]1[C:15]([O:16][CH2:17][CH3:18])=[CH:14][CH:13]=[CH:12][N:11]=1>C(O)C>[NH2:2][CH2:3][CH2:4][S:5][CH2:9][C:10]1[C:15]([O:16][CH2:17][CH3:18])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 5360545SodiumHCID 204741852-Chloromethyl-3-ethoxypyridine hydrochloride

Product 1

HCID 204022362-(2-Aminoethylthiomethyl)-3-ethoxypyridineYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Cysteamine hydrochloride (2.76 g) was added to a stirred mixture of sodium (1.576 g) in ethanol (75 cc) at 12°, 2-Chloromethyl-3-ethoxypyridine hydrochloride (4.60 g) in ethanol (70 cc) was added over 30 minutes to this mixture stirred at 10°-12°. The mixture was left to stand overnight, filtered and the filtrate was evaporated to dryness. The residue was dissolved in water, acidified to pH4 with hydrochloric acid and extracted with chloroform (discarded). The aqueous phase was adjusted to pH 12 with aqueous sodium hydroxide and was extracted with chloroform. The chloroform extracts were evaporated to give 2-(2-aminoethylthiomethyl)-3-ethoxypyridine (4.2 g) as an oil.

Workup

  1. waitThe mixture was left
  2. filtrationfiltered
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with chloroform (discarded)
  6. extractionwas extracted with chloroform
  7. customThe chloroform extracts were evaporated

Sources & evidence

ORD record
ord-fa838e6c62b449d59f9eb776ffd634fd
Source dataset
uspto-grants-1981_04
Patent number
US04264608

Reaction notes

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