Acetic Acid → 4-[Bis(4-fluorophenyl)methylene]-1-(phenylmethyl)piperidine

HRID 484715Notes

Reaction equation

HRID 484715 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)O)=[CH:4][CH:3]=1.Cl.C(O)(=O)C.O>CC1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)=[C:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 13519964alpha,alpha-Bis(4-fluorophenyl)-1-(phenylmethyl)-4-piperidinemethanol

Product 1

HCID 135199654-[Bis(4-fluorophenyl)methylene]-1-(phenylmethyl)piperidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 40 parts of α,α-bis(4-fluorophenyl)-1-(phenylmethyl)-4-piperidinemethanol, 120 parts of a hydrochloric acid solution and 50 parts of acetic acid was stirred and refluxed for 2 hours. The reaction mixture was cooled and water and methylbenzene were added: three layers were obtained. The two supernatant phases were separated and treated with ammonium hydroxide. The organic phase was separated, dried, filtered and evaporated. The residue was crystallized from 2,2'-oxybispropane, yielding 26 parts of 4-[bis(4-fluorophenyl)methylene]-1-(phenylmethyl)piperidine (intermediate 13).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. customthree layers were obtained
  4. customThe two supernatant phases were separated
  5. additiontreated with ammonium hydroxide
  6. customThe organic phase was separated
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-74ff45c5dba744e4994864b4ca504911
Source dataset
uspto-grants-1985_08
Patent number
US04533665

Reaction notes

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