Potassium Iodide → 4-{4-[(4-Chlorophenyl)(hydroxy)phenylmethyl]piperidin-1-yl}-1-(4-fluorophenyl)butan-1-one--hydrogen chloride (1/1)

HRID 1579330Notes

Reaction equation

HRID 1579330 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)=[O:27].C(=O)(O)[O-].[Na+].[I-].[K+]>C1(C)C=CC=CC=1>[ClH:1].[F:34][C:31]1[CH:30]=[CH:29][C:28]([C:26](=[O:27])[CH2:25][CH2:24][CH2:23][N:13]2[CH2:14][CH2:15][CH:10]([C:8]([OH:9])([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:11][CH2:12]2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 516892Sodium BicarbonateHCID 12795120HCID 12795120, compound

Product 1

HCID 127951214-{4-[(4-Chlorophenyl)(hydroxy)phenylmethyl]piperidin-1-yl}-1-(4-fluorophenyl)butan-1-one--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 14 g (0.0465 mole) of α-(p-chlorophenyl)-α-phenyl-4-piperidinemethanol, 12 g (0.06 mole) of 4-chloro-4'-fluorobutyrophenone, 16.8 g (0.2 mole) of sodium bicarbonate and a small amount of potassium iodide in 500 ml of toluene is refluxed 60 hours then filtered. The filtrate is concentrated to an oil which is dissoved in ether and treated with ethereal HCl. The resulting precipitate is collected and recrystallized from methanol-ethyl acetate and then methylene chloride to give 4'-fluoro-4-[4-[α-hydroxy-α-(p-chlorophenyl)benzyl]piperidino]butyrophenone hydrochloride, M.P. 154°C (dec.).

Workup

  1. filtrationthen filtered
  2. concentrationThe filtrate is concentrated to an oil which
  3. additiontreated with ethereal HCl
  4. customThe resulting precipitate is collected
  5. customrecrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-1f0bb13a0bd747a3ad183a14583aaf4f
Source dataset
uspto-grants-1976_01
Patent number
US03931197

Reaction notes

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