HCID 19968421, compound → HCID 10220867, compound

HRID 975839Notes

Reaction equation

HRID 975839 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1

Participants

3

Reactant 1

HCID 19968421HCID 19968421, compound

Product 1

HCID 10220867HCID 10220867, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5-(4-Chlorophenyl)-5-hydroxy-1-azaspiro[5.5]undecane (105.1 g) was added in portions to vigorously stirred concentrated sulphuric acid (600 ml) over 20 minutes, then the mixture was stirred at ambient temperature for a further 1 hour and poured carefully onto ice (2 l) causing a white solid to precipitate. The mixture was cooled in ice for 2 hours and the solid was collected by filtration. The solid was basified by addition to an excess of 5M aqueous sodium hydroxide solution and the product was extracted into ether (4×200 ml) followed by dichloromethane (2×250 ml). The extracts were combined, dried over sodium sulphate and the solvents removed in vacuo to give 5-(4-chlorophenyl)-1-azaspiro[5.5]undec-4-ene as a cream solid. Yield 98 g.

Workup

  1. additionpoured carefully onto ice (2 l)
  2. customto precipitate
  3. temperatureThe mixture was cooled in ice for 2 hours
  4. filtrationthe solid was collected by filtration
  5. additionThe solid was basified by addition to an excess of 5M aqueous sodium hydroxide solution
  6. extractionthe product was extracted into ether (4×200 ml)
  7. dry with materialdried over sodium sulphate
  8. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-687324b03dc347b385df4516606728b1
Source dataset
uspto-grants-1997_03
Patent number
US05610161

Reaction notes

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