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

HRID 1980127Notes

Reaction equation

HRID 1980127 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-8569a6666cd2464ab06aa3912b9540d6
Source dataset
uspto-grants-1984_11
Patent number
US04485107

Reaction notes

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