Hydrogen Bromide → HCID 23036392, compound

HRID 1709818Notes

Reaction equation

HRID 1709818 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:25]2[CH:30]=[CH:29][C:28]([Cl: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)[OH:9])=[CH:4][CH:3]=1.C1(O)C=CC=CC=1.[BrH:39]>>[OH2:9].[BrH:39].[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl: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 14407165HCID 14407165, compound

Product 1

HCID 23036392HCID 23036392, compound

Procedure

A mixture of 69.33 g (0.146 mole) of α,α-bis(4-chlorophenyl)-1-(phenylsulfonyl)-4-piperidinemethanol and 26 g (0.277 mole) of phenol in 400 ml of 48% hydrobromic acid was heated at reflux for 6 hr and then was stirred at room temperature for 10 hr. The reaction solution was decanted from a gum which had formed in the bottom of the reaction flask. The gum was washed with several portions of water and then was crystallized from ether to give a solid. The solid was recrystallized from a mixture of methanol-diethyl ether to give 26.52 g (43.6%) of white, crystalline solid, m.p. 106°-109° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hr
  3. customThe reaction solution was decanted from a gum which
  4. customhad formed in the bottom of the reaction flask
  5. washThe gum was washed with several portions of water
  6. customwas crystallized from ether
  7. customto give a solid
  8. customThe solid was recrystallized from a mixture of methanol-diethyl ether
  9. customto give 26.52 g (43.6%) of white, crystalline solid, m.p. 106°-109° C.

Sources & evidence

ORD record
ord-d671e0eed1574cffb78ab2a412bf1466
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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