Cysteamine Hydrochloride → HCID 20430498, compound

HRID 2413155Notes

Reaction equation

HRID 2413155 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[O-]CC.[Na+].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Cl>C(O)C>[CH3:10][O:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][S:5][CH2:4][CH2:3][NH2:2]

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 814952-(Chloromethyl)anisoleHCID 2723922Sodium ethoxide

Product 1

HCID 20430498HCID 20430498, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cysteamine hydrochloride (2.12 g) was added to a solution of sodium ethoxide (from 0.87 g sodium) in ethanol (50 ml) stirred under nitrogen in an ice-bath. 2-Methoxybenzyl chloride (2.93 g) was added dropwise and the mixture was stirred in an ice-bath for 0.5 hr. and allowed to stand at room temperature overnight. The mixture was evaporated to dryness. Water was added to the residue and the mixture was extracted at pH 3 with chloroform (discarded), adjusted to pH 13 and extracted a second time with chloroform. This second extract was purified by elution from silica gel with chloroform/methanolic ammonia (50:1) to give 2-(2-methoxybenzylthio)ethylamine (1.35 g) as an oil which was treated with hydrogen chloride in ethanol to give the hydrochloride m.p. 128°-30° (ethanol/ether).

Workup

  1. stirringthe mixture was stirred in an ice-bath for 0.5 hr
  2. customThe mixture was evaporated to dryness
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted at pH 3 with chloroform (discarded)
  5. extractionextracted a second time with chloroform
  6. extractionThis second extract
  7. customwas purified by elution from silica gel with chloroform/methanolic ammonia (50:1)

Sources & evidence

ORD record
ord-c526c17bd19d4ab18c164682f80138ab
Source dataset
uspto-grants-1985_01
Patent number
US04496567

Reaction notes

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