HCID 11043960, compound → 184638-09-3

HRID 1457313Notes

Reaction equation

HRID 1457313 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8](O)[CH:7]([CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:6][CH2:5]2>Cl.C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]=[C:7]([CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:6][CH2:5]2

Participants

4

Reactant 1

HCID 11043960HCID 11043960, compound

Product 1

HCID 9816524184638-09-3Yield 64.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

1,2,3,4-Tetrahydro-6,7-dimethyl-2-[2-(1-pyrrolidinyl)ethyl]-1-naphthalenol (24.0 g) was dissolved in a 30% solution of hydrogen chloride in ethanol (240 ml), and the mixture was refluxed for one hour. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in water. The mixture was basified with potassium carbonate, and extracted with ethyl acetate. The extract was washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol=10:1), and the fractions containing the desired compound were combined, and concentrated under reduced pressure to give the desired compound (14.5 g) as an oily product.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol=10:1)
  10. additionthe fractions containing the desired compound
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f2a53f529d846e88928e0569a00cb58
Source dataset
uspto-grants-1998_12
Patent number
US05847159

Reaction notes

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