Hydrochloric Acid → HCID 13363247, compound

HRID 1980144Notes

Reaction equation

HRID 1980144 reaction equation
O[C:2]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:3]1[CH2:8][CH2:7][N:6](C(OCC)=O)[CH2:5][CH2:4]1.Cl>C(O)C>[C:14]1([C:2](=[C:3]2[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]2)[C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53726868HCID 53726868, compound

Product 1

HCID 13363247HCID 13363247, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 106 parts of ethyl 4-[hydroxy(4-methoxyphenyl)-phenylmethyl]-1-piperidinecarboxylate, 1200 parts of concentrate hydrochloric acid and 200 parts of ethanol was stirred and refluxed for 18 hours. Gazeous hydrogen chloride was bubbled through the mixture and stirring was continued for 18 hours at reflux temperature. The whole was evaporated. The residue was dissolved in a mixture of 200 parts of ethanol and 1950 parts of a hydrobromic acid solution 48% in water. The mixture was stirred and refluxed overnight. After evaporating, the residue was suspended in 1000 parts of water and treated with ammonium hydroxide. The oil was dissolved in 2100 parts of trichloromethane. The solution was washed with 500 parts of water, dried, filtered and evaporated. The residue was suspended three times in 70 parts of 2,2'-oxybispropane and the latter was evaporated each time. The residue was solidified in 40 parts of acetonitrile. The product was filtered off and dried, yielding 20 parts (25%) of 4-[phenyl(4-piperidinylidene)methyl]phenol; mp.>260° C. (intermediate 32).

Workup

  1. temperaturerefluxed for 18 hours
  2. customGazeous hydrogen chloride was bubbled through the mixture
  3. stirringstirring
  4. temperatureat reflux temperature
  5. customThe whole was evaporated
  6. dissolutionThe residue was dissolved in a mixture of 200 parts of ethanol and 1950 parts of a hydrobromic acid solution 48% in water
  7. stirringThe mixture was stirred
  8. temperaturerefluxed overnight
  9. customAfter evaporating
  10. additiontreated with ammonium hydroxide
  11. dissolutionThe oil was dissolved in 2100 parts of trichloromethane
  12. washThe solution was washed with 500 parts of water
  13. customdried
  14. filtrationfiltered
  15. customevaporated
  16. customthe latter was evaporated each time
  17. filtrationThe product was filtered off
  18. customdried

Sources & evidence

ORD record
ord-25608b3fb7144dd6ba55c77eee66ae4e
Source dataset
uspto-grants-1984_11
Patent number
US04485107

Reaction notes

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