Hydrogen Bromide → HCID 19968418, compound

HRID 975832Notes

Reaction equation

HRID 975832 reaction equation
[ClH:1].C[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]3([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[NH:14][CH2:13][CH2:12][CH:11]=2)=[CH:6][CH:5]=1.Br.C(=O)([O-])O.[Na+]>C(O)(=O)C>[ClH:1].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]3([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)[NH:14][CH2:13][CH2:12][CH:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 19968436HCID 19968436, compound

Product 1

HCID 19968418HCID 19968418, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-(4-methoxyphenyl)-1-azaspiro[5.5]undec-4-ene hydrochloride (1.0 g), glacial acetic acid (20 ml) and hydrobromic acid (48%, 20 ml) was heated under reflux for 6.5 hours then allowed to cool. The mixture was neutralised by the addition of saturated aqueous sodium hydrogen carbonate solution and the product extracted into ether (3×100 ml). The extracts were combined, dried over magnesium sulphate and the solvent removed in vacuo to give a solid which was purified via flash chromatography over silica using toluene/triethylamine (4:1) as eluent. Appropriate fractions were combined, the solvents were removed in vacuo, and the resulting product was dissolved in ether. The solution was filtered, and the filtrate cooled in ice and saturated with hydrogen chloride. The resulting solid was collected by filtration, washed with ether and dried in vacuo at ambient temperature to give 5-(4-hydroxyphenyl)-1-azaspiro[5.5]undec-4-ene hydrochloride as a white solid. Yield 0.7 g, mp 285°-295° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6.5 hours
  3. temperatureto cool
  4. extractionthe product extracted into ether (3×100 ml)
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed in vacuo
  7. customto give a solid which
  8. customwas purified via flash chromatography over silica
  9. customthe solvents were removed in vacuo
  10. dissolutionthe resulting product was dissolved in ether
  11. filtrationThe solution was filtered
  12. temperaturethe filtrate cooled in ice and saturated with hydrogen chloride
  13. filtrationThe resulting solid was collected by filtration
  14. washwashed with ether
  15. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-4af70677b3be4925b0e655c9ce68260e
Source dataset
uspto-grants-1997_03
Patent number
US05610161

Reaction notes

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