Potassium Iodide → HCID 21528611, compound

HRID 1658662Notes

Reaction equation

HRID 1658662 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:21][CH2:22][CH2:23][CH2:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)=[O:26].C(=O)(O)[O-].[Na+].[I-].[K+]>C1(C)C=CC=CC=1>[ClH:21].[OH:8][C:7]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:22][CH2:23][CH2:24][C:25]([C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)=[O:26])[CH2:11][CH2:10]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 15723AzacyclonolHCID 987454-Chloro-4'-methylbutyrophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 21528611HCID 21528611, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 53.5 g (0.2 moles) of α,α -diphenyl-4-piperidinemethanol 43.3 g (0.22 mole) of 4-chloro-4'-methylbutyrophenone, 33.6 g (0.4 mole) of sodium bicarbonate and a small amount of potassium iodide in 1300 ml of toluene was refluxed for 17 hours collecting the evolved water in a Dean-Stark trap. The mixture was filtered and the solvent removed. The residue was dissolved in ether and treated with ethereal HCl, and the resulting precipitate was washed with dry ether and recrystallized from ethyl acetate-methanol and from isopropyl alcohol to give the desired product, M.P. 236°-237° C.

Workup

  1. customcollecting the evolved water in a Dean-Stark trap
  2. filtrationThe mixture was filtered
  3. customthe solvent removed
  4. dissolutionThe residue was dissolved in ether
  5. additiontreated with ethereal HCl
  6. washthe resulting precipitate was washed with dry ether
  7. customrecrystallized from ethyl acetate-methanol and from isopropyl alcohol

Sources & evidence

ORD record
ord-e0d3998fe0394c64ba41ad8343317d5f
Source dataset
uspto-grants-1976_06
Patent number
US03965257

Reaction notes

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