Potassium Iodide → 1-(4-tert-Butylphenyl)-4-{4-[hydroxy(diphenyl)methyl]piperidin-1-yl}butan-1-one--hydrogen chloride (1/1)

HRID 1658663Notes

Reaction equation

HRID 1658663 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.[C:21]([C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:36])[CH2:32][CH2:33][CH2:34][Cl:35])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1>[ClH:35].[C:21]([C:25]1[CH:26]=[CH:27][C:28]([C:31](=[O:36])[CH2:32][CH2:33][CH2:34][N:12]2[CH2:13][CH2:14][CH:9]([C:7]([OH:8])([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:10][CH2:11]2)=[CH:29][CH:30]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 15723AzacyclonolHCID 516893Potassium BicarbonateHCID 27236944'-tert-Butyl-4-chlorobutyrophenone

Product 1

HCID 127951221-(4-tert-Butylphenyl)-4-{4-[hydroxy(diphenyl)methyl]piperidin-1-yl}butan-1-one--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 107 g (0.4 mole) of α,α -diphenyl-4-piperidinemethanol, 105 g (0.44 mole) of 4' -tert-butyl-4-chlorobutyrophenone, 70 g (0.7 mole) of potassium bicarbonate, and a small amount of potassium iodide in 600 ml of toluene was refluxed and stirred for 21/2 days then filtered. The filtrate was treated with charcoal, filtered through celite then treated with ethereal HCl. The resulting solid was recrystallized from methanol and isopropyl alcohol to give the desired product, M.P. 234°-235° C.

Workup

  1. filtrationthen filtered
  2. additionThe filtrate was treated with charcoal
  3. filtrationfiltered through celite
  4. additionthen treated with ethereal HCl
  5. customThe resulting solid was recrystallized from methanol and isopropyl alcohol

Sources & evidence

ORD record
ord-44d40c3bbc8b4091b50ba9e03fb52569
Source dataset
uspto-grants-1976_06
Patent number
US03965257

Reaction notes

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