Sulfuric Acid → HCID 19968428, compound

HRID 975831Notes

Reaction equation

HRID 975831 reaction equation
[F: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:20](=[O:24])(=[O:23])([OH:22])[OH:21]>>[S:20]([OH:24])([OH:23])(=[O:22])=[O:21].[F: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 2

HCID 1118Sulfuric AcidHCID 19968450HCID 19968450, compound

Product 1

HCID 19968428HCID 19968428, compound

Procedure

5-(4-Fluorophenyl)-5-hydroxy-1-azaspiro[5.5]undecane (1.27 g, prepared in a similar manner to that described in Example F) was dissolved in concentrated sulphuric acid (25 ml) and stirred at ambient temperature for 2 hours, then the solution was carefully poured onto ice (50 ml), and the sticky solid collected by filtration. The solid was triturated with ether (2×50 ml), collected by filtration, washed with ether and dried in vacuo at ambient temperature to give a solid which was triturated with hot ether (70 ml), collected by filtration washed with ether and dried in vacuo at 60° C. to give 5-(4-fluorophenyl)-1-azaspiro[5.5]undec-4-ene sulphate as a white solid. Yield 1.3 g, mp 195°-200° C.

Workup

  1. additionthe solution was carefully poured onto ice (50 ml)
  2. filtrationthe sticky solid collected by filtration
  3. customThe solid was triturated with ether (2×50 ml)
  4. filtrationcollected by filtration
  5. washwashed with ether
  6. customdried in vacuo at ambient temperature
  7. customto give a solid which
  8. customwas triturated with hot ether (70 ml)
  9. filtrationcollected by filtration
  10. washwashed with ether
  11. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-1c2031aa19e148f3a6551b7c96dc4517
Source dataset
uspto-grants-1997_03
Patent number
US05610161

Reaction notes

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