Cysteamine Hydrochloride → 2-[(6-Dimethylaminomethyl-2-pyridyl)methylthio]ethylamine

HRID 1702318Notes

Reaction equation

HRID 1702318 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[CH3:6][N:7]([CH2:9][C:10]1[N:15]=[C:14]([CH2:16]O)[CH:13]=[CH:12][CH:11]=1)[CH3:8]>Br>[CH3:6][N:7]([CH2:9][C:10]1[N:15]=[C:14]([CH2:16][S:5][CH2:4][CH2:3][NH2:2])[CH:13]=[CH:12][CH:11]=1)[CH3:8]

Participants

4

Reactant 2

HCID 9082Cysteamine HydrochlorideHCID 155923006-Dimethylaminomethyl-2-hydroxymethylpyridine

Product 1

HCID 212920152-[(6-Dimethylaminomethyl-2-pyridyl)methylthio]ethylamineYield 46.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Cysteamine hydrochloride (3.58 g; 31.5 mmoles) and 6-dimethylaminomethyl-2-hydroxymethylpyridine (5.0 g; 30.1 mmole) [prepared in Step B] were dissolved in 50 ml of 48% hydrobromic acid and the solution heated at reflux temperature for 12 hours and then allowed to stand at ambient temperature for 8 hours. The reaction mixture was evaporated under reduced pressure to half volume, made basic with 40% aqueous NaOH and extracted with several portions of methylene chloride. The combined organic phase was washed with a small amount of water and saturated brine solution then dried and evaporated under reduced pressure to yield 3.14 g of the title compound.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux temperature for 12 hours
  3. customThe reaction mixture was evaporated under reduced pressure to half volume
  4. extractionextracted with several portions of methylene chloride
  5. washThe combined organic phase was washed with a small amount of water and saturated brine solution
  6. customthen dried
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d72eaa8de27f45ed84dfd58f19632404
Source dataset
uspto-grants-1983_04
Patent number
US04380638

Reaction notes

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