2-(Dimethylamino)ethanol → N,N-Dimethyl-2-[(3-phenylquinolin-2-yl)oxy]ethan-1-amine--hydrogen chloride (1/1)

HRID 364912Notes

Reaction equation

HRID 364912 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[H][H].[Cl:11][C:12]1[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1>CN(C)C=O>[ClH:11].[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:12]1[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 42560782-Chloro-3-phenylquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 20238626N,N-Dimethyl-2-[(3-phenylquinolin-2-yl)oxy]ethan-1-amine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Dimethylaminoethanol (1.07 g.) was added dropwise to a suspension of sodium hydride (0.56 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (25 ml.) at 0°-5°. When all the hydrogen had evolved, 2-chloro-3-phenylquinoline (2.5 g.) was added and the mixture was stirred and heated at 75° for 12 hours. The mixture was then cooled to ambient temperature, poured into ice-water (500 ml.), and extracted with ethyl acetate (5×100 ml.). The ethyl acetate extract was washed successively with water (50 ml.) and saturated brine (50 ml.), and then dried (MgSO4). The solvent was evaporated under reduced pressure (approx. 15 mm.) and the residual oil was chromatographed on basic alumina (100 g.; Brockmann Grade III), eluted with increasing concentrations of chloroform in petroleum ether. The eluate obtained with 10% v/v chloroform in petroleum ether was evaporated. The residual oil was dissolved in diethyl ether (100 ml.), and ethereal hydrogen chloride was added until precipitation was complete The mixture was filtered and the solid residue was crystallised from ethanol-diethyl ether to give 2-(2-dimethylaminoethoxy)-3-phenylquinoline hydrochloride, m.p. 155°-7°.

Workup

  1. customat 0°-5°
  2. temperatureheated at 75° for 12 hours
  3. extractionextracted with ethyl acetate (5×100 ml.)
  4. extractionThe ethyl acetate extract
  5. washwas washed successively with water (50 ml.) and saturated brine (50 ml.)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated under reduced pressure (approx. 15 mm.)
  8. customthe residual oil was chromatographed on basic alumina (100 g.; Brockmann Grade III)
  9. washeluted
  10. temperaturewith increasing concentrations of chloroform in petroleum ether
  11. customThe eluate obtained with 10% v/v chloroform in petroleum ether
  12. customwas evaporated
  13. dissolutionThe residual oil was dissolved in diethyl ether (100 ml.)
  14. additionethereal hydrogen chloride was added until precipitation
  15. filtrationwas filtered
  16. customthe solid residue was crystallised from ethanol-diethyl ether

Sources & evidence

ORD record
ord-739136f3fd694791a639c4b1a63901d8
Source dataset
uspto-grants-1986_08
Patent number
US04607040

Reaction notes

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