HCID 19968441, compound → HCID 11779419, compound

HRID 975829Notes

Reaction equation

HRID 975829 reaction equation
S(O)(O)(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18]3([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[NH:17][CH2:16][CH2:15][CH:14]=2)=[CH:9][CH:8]=1>[OH-].[Na+]>[ClH:6].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18]3([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[NH:17][CH2:16][CH2:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

3

Reactant 1

HCID 19968441HCID 19968441, compound

Product 1

HCID 11779419HCID 11779419, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 5-(4-chlorophenyl)-1-azaspiro[5.5]undec-4-ene sulphate (13 g prepared in a similar manner to that described in Example 5) in 1M aqueous sodium hydroxide solution (200 ml) was stirred at ambient temperature for 1 hour, then the free base was extracted into ether (3×150 ml). The extracts were combined, dried over magnesium sulphate, concentrated to a volume of 150 ml, and filtered. The filtrate was 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 for 24 hours and at 60° C. for 8 hours to give 5-(4-chlorophenyl)-1-azaspiro[5.5]undec-4-ene hydrochloride as a white solid. Yield 8.6 g, mp >300° C.

Workup

  1. customprepared in a similar manner to that
  2. extractionthe free base was extracted into ether (3×150 ml)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to a volume of 150 ml
  5. filtrationfiltered
  6. temperatureThe filtrate was cooled in ice and saturated with hydrogen chloride
  7. filtrationThe resulting solid was collected by filtration
  8. washwashed with ether
  9. customdried in vacuo at ambient temperature for 24 hours and at 60° C. for 8 hours

Sources & evidence

ORD record
ord-de1eb73209b64ad9adec0142c9690f70
Source dataset
uspto-grants-1997_03
Patent number
US05610161

Reaction notes

Loading…