Potassium Iodide → 4-[4-(6-Chloro-2-naphthoyl)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone

HRID 1389876Notes

Reaction equation

HRID 1389876 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:20])[CH:16]=3)[CH:11]=2)=[O:9])[CH2:4][CH2:3]1.Cl[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].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1>[Cl:20][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:8]([CH:5]1[CH2:6][CH2:7][N:2]([CH2:22][CH2:23][CH2:24][C:25]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[O:26])[CH2:3][CH2:4]1)=[O:9])[CH:19]=[CH:18]2

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 516893Potassium BicarbonateHCID 705701616-Chloro-2-naphthyl 4-piperidyl ketone hydrochloride

Product 1

HCID 202956124-[4-(6-Chloro-2-naphthoyl)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.43 g (12.5 mmoles) of 6-chloro-2-naphthyl 4-piperidyl ketone hydrochloride, 2.63 g (13.1 mmoles) of 4-chloro-1-(4-fluorophenyl)-1-butanone, 2.6 g (26 mmoles) 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-(6-chloro-2-naphthoyl)-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-f86c3843cd534d10a41d1dcda6c13f9f
Source dataset
uspto-grants-1981_01
Patent number
US04246268

Reaction notes

Loading…