Hydrochloric Acid → 4-[Bis-(4-fluorophenyl)methylene]piperidine hydrochloride

HRID 1584803Notes

Reaction equation

HRID 1584803 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)([CH:10]2[CH2:15][CH2:14][N:13](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:12][CH2:11]2)O)=[CH:4][CH:3]=1.[ClH:42]>>[ClH:42].[F:41][C:38]1[CH:39]=[CH:40][C:35]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[C:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 13504544alpha,alpha-Bis-(4-fluorophenyl)-1-(triphenylmethyl)-4-piperidinemethanol

Product 1

HCID 133631904-[Bis-(4-fluorophenyl)methylene]piperidine hydrochloride

Procedure

α,α-Bis-(4-fluorophenyl)-1-(triphenylmethyl)-4-piperidinemethanol (67 g; 0.123 mol) was dissolved in hydrochloric acid (1 l; 2 mol/l) and the solution was heated under reflux for 2 h. The solution was cooled, the precipitated solid was collected by filtration and suspended in anhydrous diethyl ether. The mixture was stirred for 1 h, filtered and the solid was crystallised from methanol/ether to give the product (28.3 g) as white crystals; m.p. 83° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 2 h
  3. temperatureThe solution was cooled
  4. filtrationthe precipitated solid was collected by filtration
  5. filtrationfiltered
  6. customthe solid was crystallised from methanol/ether

Sources & evidence

ORD record
ord-63e33594fbdd468493d5dce8ce64ac66
Source dataset
uspto-grants-1999_08
Patent number
US05935974

Reaction notes

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