Hydrogen Bromide → 4-[Bis(4-Fluorophenyl)methylene]piperidine hydrobromide

HRID 1709810Notes

Reaction equation

HRID 1709810 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)([CH:10]2[CH2:15][CH2:14][N:13](S(C3C=CC=CC=3)(=O)=O)[CH2:12][CH2:11]2)O)=[CH:4][CH:3]=1.C1(O)C=CC=CC=1.[BrH:39]>>[BrH:39].[F:31][C:28]1[CH:29]=[CH:30][C:25]([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:26][CH:27]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 14407073alpha,alpha-Bis(4-fluorophenyl)-1-(phenylsulfonyl)-4-piperidinemethanol

Product 1

HCID 191008874-[Bis(4-Fluorophenyl)methylene]piperidine hydrobromide

Procedure

A mixture of 164 g (0.342 mole) of α,α-bis(4-fluorophenyl)-1-(phenylsulfonyl)-4-piperidinemethanol and 80 g (80 g) of phenol in 700 ml of 48% hydrobromic acid was heated at reflux for 7 hr and then was stirred at room temperature for 9 hr. The hydrobromic acid solution was decanted from a gum in the bottom of the reaction flask. The gum was triturated with ~1 liter of ether, and a tan solid formed. The solid was washed with several portions of ether and was dried under high vacuum to give 9.13 g (73%) of slightly impure title product, m.p. 211°-215° C. A small sample of this solid was recrystallized from methanol to give an analytically pure sample as a crystalline solid; m.p. 216°-218° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hr
  3. customThe hydrobromic acid solution was decanted from a gum in the bottom of the reaction flask
  4. customThe gum was triturated with ~1 liter of ether
  5. customa tan solid formed
  6. washThe solid was washed with several portions of ether
  7. customwas dried under high vacuum

Sources & evidence

ORD record
ord-dcf96df185b849b1a9ce3c87f1be3591
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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