Potassium Iodide → 1-Butanone, 1-(4-fluorophenyl)-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-, hydrochloride

HRID 1658658Notes

Reaction equation

HRID 1658658 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]([F:33])=[CH:29][CH:28]=1)=[O:26].[I-].[K+].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[ClH:21].[F:33][C:30]1[CH:29]=[CH:28][C:27]([C:25](=[O:26])[CH2:24][CH2:23][CH2:22][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:32][CH:31]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 15723AzacyclonolHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 2061821-Butanone, 1-(4-fluorophenyl)-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-, hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 26.73 g (0.1 mole) of α,α -diphenyl-4-piperidinemethanol, 22 g (0.11 mole) of 4-chloro-4' -fluorobutyrophenone, a trace of potassium iodide and 13.5 g (0.16 mole) of sodium bicarbonate in 500 ml of toluene was refluxed for 21/2 days. The mixture was filtered, and the filtrate was cooled. The resulting solid was converted by generally known methods to the hydrochloride salt which was recrystallized from methanol and butanone to give the desired product, M.P. 224.5°-225.5° C.

Workup

  1. filtrationThe mixture was filtered
  2. temperaturethe filtrate was cooled
  3. customwas recrystallized from methanol and butanone

Sources & evidence

ORD record
ord-f908f56bbab342eea966ce478e33b3bd
Source dataset
uspto-grants-1976_06
Patent number
US03965257

Reaction notes

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