Methyl iodide → Ethanamine, N,N-dimethyl-2-((3-phenyl-2-quinolinyl)thio)-, hydrochloride (1:1)

HRID 1903240Notes

Reaction equation

HRID 1903240 reaction equation
CI.[ClH:3].[CH3:4][NH:5][CH2:6][CH2:7][S:8][C:9]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[C:25](=O)([O-])[O-].[K+].[K+]>C(O)C>[ClH:3].[CH3:4][N:5]([CH3:25])[CH2:6][CH2:7][S:8][C:9]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 132002082-(2-Methylaminoethylthio)-3-phenylquinoline hydrochloride

Product 1

HCID 174433Ethanamine, N,N-dimethyl-2-((3-phenyl-2-quinolinyl)thio)-, hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl iodide (0.85 g.) was added to a mixture of 2-(2-methylaminoethylthio)-3-phenylquinoline hydrochloride (1.65 g.) and potassium carbonate (1.65 g.) in dry ethanol (50 ml.) at ambient temperature. The mixture was stirred at ambient temperature for 3 hr. and the solvent was then evaporated. The residue was dissolved in water (50 ml.) and extracted with diethyl ether (3×25 ml.). The diethyl ether extract was washed with brine (25 ml.), dried (MgSO4), and the solvent evaporated. The residual oil was chromatographed on basic alumina (75 g., Brockmann Grade III), eluted with increasing concentrations of methylene dichloride in petroleum ether. The eluate with 50% v/v methylene dichloride in petroleum ether was evaporated. The residue was dissolved in diethyl ether (25 ml.) and ethereal hydrogen chloride added until precipitation was complete. The mixture was filtered and the solid residue was crystallised from methanol-ethyl acetate to give 2-(2-dimethylaminoethylthio)-3-phenylquinoline hydrochloride, m.p. 196°-8°.

Workup

  1. customand the solvent was then evaporated
  2. dissolutionThe residue was dissolved in water (50 ml.)
  3. extractionextracted with diethyl ether (3×25 ml.)
  4. extractionThe diethyl ether extract
  5. washwas washed with brine (25 ml.)
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated
  8. customThe residual oil was chromatographed on basic alumina (75 g., Brockmann Grade III)
  9. washeluted
  10. temperaturewith increasing concentrations of methylene dichloride in petroleum ether
  11. customThe eluate with 50% v/v methylene dichloride in petroleum ether was evaporated
  12. dissolutionThe residue was dissolved in diethyl ether (25 ml.)
  13. additionethereal hydrogen chloride added until precipitation
  14. filtrationThe mixture was filtered
  15. customthe solid residue was crystallised from methanol-ethyl acetate

Sources & evidence

ORD record
ord-92cd2758a07d4d6cb5cb718ba977b27a
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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