HCID 19968447, compound → HCID 19968433, compound

HRID 975830Notes

Reaction equation

HRID 975830 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2(O)[C:13]3([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[NH:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1>S(=O)(=O)(O)O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[NH:12][CH2:11][CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 19968447HCID 19968447, compound

Product 1

HCID 19968433HCID 19968433, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5-(3-Chlorophenyl)-5-hydroxy-1-azaspiro[5.5]undecane (2.5 g, prepared as described in Example D) was dissolved in concentrated sulphuric acid (35 ml) and stirred at ambient temperature for 2 hours. The mixture was then poured cautiously onto ice (100 ml) and the resulting white precipitate was collected by filtration and suspended in ethyl acetate (300 ml). 5M Aqueous sodium hydroxide solution (250 ml) was added and the mixture was stirred at ambient temperature for 15 minutes. The aqueous layer was separated and extracted with ethyl acetate (2×200 ml), then the combined organic solutions were washed with water, dried over magnesium sulphate and the solvent removed in vacuo. The resulting oil was dissolved in ether (100 ml), charcoal (1 g) was added, and the mixture was heated under reflux for 5 minutes and hot-filtered. The cooled filtrate was saturated with hydrogen chloride and the resulting solid collected, washed with ether and dried in vacuo at ambient temperature to give 5-(3-chlorophenyl)-1-azaspiro[5.5]undec-4-ene hydrochloride as a white solid. Yield 2.1 g, mp 281°-282° C. (dec).

Workup

  1. additionThe mixture was then poured cautiously onto ice (100 ml)
  2. filtrationthe resulting white precipitate was collected by filtration
  3. addition5M Aqueous sodium hydroxide solution (250 ml) was added
  4. stirringthe mixture was stirred at ambient temperature for 15 minutes
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate (2×200 ml)
  7. washthe combined organic solutions were washed with water
  8. dry with materialdried over magnesium sulphate
  9. customthe solvent removed in vacuo
  10. dissolutionThe resulting oil was dissolved in ether (100 ml)
  11. additioncharcoal (1 g) was added
  12. temperaturethe mixture was heated
  13. temperatureunder reflux for 5 minutes
  14. filtrationhot-filtered
  15. customthe resulting solid collected
  16. washwashed with ether
  17. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-b6508743addc42519caed2809695686a
Source dataset
uspto-grants-1997_03
Patent number
US05610161

Reaction notes

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