HCID 19968443, compound → HCID 19968454, compound

HRID 975841Notes

Reaction equation

HRID 975841 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:12]3([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>S(=O)(=O)(O)O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[NH:11][CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 19968443HCID 19968443, compound

Product 1

HCID 19968454HCID 19968454, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The crude 4-(4-chlorophenyl)-4-hydroxy-1azaspiro[4.5]decane (2.2 g) was dissolved in concentrated sulphuric acid (27 ml) and the solution was stirred at ambient temperature for 1 hour. The mixture was poured onto ice to give a white precipitate which was collected by filtration, dissolved in water, and basified by the addition of 5M aqueous sodium hydroxide solution. The product was extracted into ether (3×200 ml) and the extracts were combined, dried over magnesium sulphate, and concentrated in vacuo to 100 ml. The solution was saturated with hydrogen chloride and the resulting solid was collected by filtration and dried in vacuo at 60° C. for 7 hours to give 4-(4-chlorophenyl)-1-azaspiro[4.5]dec-3-ene hydrochloride as a white solid. Yield 1.1 g, mp 225°-233° C.(dec).

Workup

  1. additionThe mixture was poured onto ice
  2. customto give a white precipitate which
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in water
  5. additionbasified by the addition of 5M aqueous sodium hydroxide solution
  6. extractionThe product was extracted into ether (3×200 ml)
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated in vacuo to 100 ml
  9. filtrationthe resulting solid was collected by filtration
  10. customdried in vacuo at 60° C. for 7 hours

Sources & evidence

ORD record
ord-c5bc8ecce16c4502bdf9af69b55a6220
Source dataset
uspto-grants-1997_03
Patent number
US05610161

Reaction notes

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