Hydrochloric Acid → HCID 70577204, compound

HRID 2286909Notes

Reaction equation

HRID 2286909 reaction equation
O(C([N:10]1[CH2:15][CH2:14][C:13]2([C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:22][C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:12][CH2:11]1)=O)C1C=CC=CC=1.C(O)C.[OH-].[K+].[ClH:34]>O>[ClH:34].[NH:10]1[CH2:11][CH2:12][C:13]2([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[O:22][C:23]3[C:28]2=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 70577728HCID 70577728, compound

Product 1

HCID 70577204HCID 70577204, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1'-phenoxycarbonylxanthene-9-spiro-4'-piperidine (370 mg.), ethanol (80 ml.) and a 50% w/v solution of potassium hydroxide in water (20 ml.) is heated under reflux for 22 hours. The mixture is cooled and concentrated hydrochloric acid (20 ml.) is added and the ethanol is evaporated. The residue is washed with ether, water (50 ml.) is added and the resulting solution made alkaline with 3 N sodium hydroxide. The alkaline solution is extracted with chloroform and the chloroform extract is washed with water, dried (MgSO4) and evaporated to dryness. The gummy residue is dissolved in ethanol and treated with ethereal hydrochloric acid. The solid is recrystallised from ethanol-ether to give xanthene-9-spiro-4'-piperidine hydrochloride, m.p. 248°-250° C.

Workup

  1. temperatureunder reflux for 22 hours
  2. temperatureThe mixture is cooled
  3. customthe ethanol is evaporated
  4. washThe residue is washed with ether, water (50 ml.)
  5. additionis added
  6. extractionThe alkaline solution is extracted with chloroform
  7. extractionthe chloroform extract
  8. washis washed with water
  9. dry with materialdried (MgSO4)
  10. customevaporated to dryness
  11. dissolutionThe gummy residue is dissolved in ethanol
  12. additiontreated with ethereal hydrochloric acid
  13. customThe solid is recrystallised from ethanol-ether

Sources & evidence

ORD record
ord-54ba1c62ed8d4da5b0bb80f422c8527c
Source dataset
uspto-grants-1981_05
Patent number
US04268514

Reaction notes

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