HCID 21285457, compound → Hydrochloric Acid

HRID 364984Notes

Reaction equation

HRID 364984 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][N:12]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.CO.[C:26]([O:29][CH2:30]C)(=[O:28])C>Br>[ClH:1].[ClH:1].[CH3:30][O:29][C:26](=[O:28])[CH2:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][N:12]2[CH2:11][CH2:10][O:9][CH:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH2:13]2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 21285457HCID 21285457, compoundHCID 21584119Ethylacetate methanol

Product 2

HCID 313Hydrochloric AcidHCID 70409412HCID 70409412, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 4-[2-(2-[3-chlorophenyl]morpholino)ethyl]anisole (2.6 g) in 48% aqueous hydrobromic acid (90 ml) was heated under reflux, with stirring, for 4 hours, cooled and evaporated to dryness. The residue was dissolved in acetone (80 ml), added to a mixture of anhydrous potassium carbonate (11 g), potassium iodide (50 mg) and methyl bromoacetate (1.5 ml) and the resultant mixture heated under reflux, with stirring, overnight. After cooling, filtering and evaporating the filtrate to dryness, the residue was dissolved in dichloromethane, washed with aqueous sodium carbonate (×2), brine (×1), dried (MgSO4), filtered and evaporated to dryness. Chromatography of the residue on silica gel in 0-2% methanol in dichloromethane gave an oil, which, on treatment with an ethereal solution of hydrogen chloride, gave the title compound, m.p. 156°-7° C. (methanol-ethyl acetate).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in acetone (80 ml)
  6. additionadded to a mixture of anhydrous potassium carbonate (11 g), potassium iodide (50 mg) and methyl bromoacetate (1.5 ml)
  7. temperaturethe resultant mixture heated
  8. temperatureunder reflux
  9. stirringwith stirring, overnight
  10. temperatureAfter cooling
  11. filtrationfiltering
  12. customevaporating the filtrate to dryness
  13. dissolutionthe residue was dissolved in dichloromethane
  14. washwashed with aqueous sodium carbonate (×2), brine (×1)
  15. dry with materialdried (MgSO4)
  16. filtrationfiltered
  17. customevaporated to dryness
  18. customChromatography of the residue on silica gel in 0-2% methanol in dichloromethane gave an oil, which

Sources & evidence

ORD record
ord-b8ec60efb58a41459f86083eef7ee1d3
Source dataset
uspto-grants-1986_08
Patent number
US04607033

Reaction notes

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