Potassium Iodide → 4-[4-(1-Methyl-2-naphthalenyloxy)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone

HRID 325964Notes

Reaction equation

HRID 325964 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.Cl[CH2:20][CH2:21][CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=[O:24].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:20][CH2:21][CH2:22][C:23]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[O:24])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 516893Potassium BicarbonateHCID 204632094-(1-Methyl-2-naphthalenyloxy)piperidine

Product 1

HCID 204632324-[4-(1-Methyl-2-naphthalenyloxy)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.47 g of (12.5 mmole) of 4-(1-methyl-2-naphthalenyloxy)piperidine, 2.63 g (13.1 mmole) of 4-chloro-1-(4-fluorophenyl)-1-butanone, 5.2 g (52 mmole) of potassium bicarbonate and a pinch of potassium iodide in 60 ml of toluene is heated at reflux for 80 hours. The mixture is partitioned between toluene and water and the organic phase washed with brine, dried over magnesium sulfate, and concentrated in vacuo to yield 4-[4-(1-methyl-2-naphthalenyloxy)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone.

Workup

  1. temperatureat reflux for 80 hours
  2. customThe mixture is partitioned between toluene and water
  3. washthe organic phase washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40f9672771934035aac58d8d08440ecf
Source dataset
uspto-grants-1984_04
Patent number
US04443462

Reaction notes

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