Hydrochloric Acid → HCID 23326067, compound

HRID 1380242Notes

Reaction equation

HRID 1380242 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)O)[CH2:6][CH2:5]1)(=O)C.[ClH:26]>C(O)C>[ClH:26].[Br:25][C:22]1[CH:23]=[CH:24][C:19]([C:10]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[C:7]2[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23326078HCID 23326078, compound

Product 1

HCID 23326067HCID 23326067, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 75 parts of 1-acetyl-α-(4-bromophenyl)-α-(4-fluorophenyl)-4-piperidinemethanol, 600 parts of concentrate hydrochloric acid and 80 parts of ethanol was stirred and refluxed for 18 hours. The reaction mixture was evaporated. 500 Parts of water were added to the residue. The solution was treated with ammonium hydroxide. The product was extracted twice with 375 parts of trichloromethane. The combined organic layers were washed with 100 parts of water, dried, filtered and evaporated. The oily residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume), saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol. The whole was evaporated. The residue solidified in 80 parts of acetonitrile. The product was filtered off (filtrate I was set aside) and crystallized from 160 parts of acetonitrile at 0° C. The product was filtered off (filtrate II was set aside) and dried, yielding 36 parts of 4-[(4-bromophenyl)(4-fluorophenyl)methylene]-piperidine hydrochloride. Filtrate I and filtrate II which were set aside (see above), were concentrated to a volume of 40 parts. The concentrate was allowed to crystallize. The product was filtered off and dried, yielding 4 parts of 4-[(4-bromophenyl)(4-fluorophenyl)methylene]piperidine hydrochloride.

Workup

  1. temperaturerefluxed for 18 hours
  2. customThe reaction mixture was evaporated
  3. addition500 Parts of water were added to the residue
  4. additionThe solution was treated with ammonium hydroxide
  5. extractionThe product was extracted twice with 375 parts of trichloromethane
  6. washThe combined organic layers were washed with 100 parts of water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe oily residue was purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (90:10 by volume)
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated
  14. customThe whole was evaporated
  15. filtrationThe product was filtered off (filtrate I
  16. customcrystallized from 160 parts of acetonitrile at 0° C
  17. filtrationThe product was filtered off (filtrate II
  18. customdried

Sources & evidence

ORD record
ord-e1668bd39651445f91145513c2982b8a
Source dataset
uspto-grants-1986_04
Patent number
US04581171

Reaction notes

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