Potassium Iodide → 5-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-5-oxo-pentanoic Acid Ethyl Ester

HRID 11712

Reaction equation

HRID 11712 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:7][CH:6]1[CH3:20])=[O:4].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:29]([O:31][C:32](=[O:46])[CH2:33][CH2:34][CH2:35][C:36]([C:38]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:39]=1[OH:45])=[O:37])[CH3:30]>CC(=O)CC>[CH2:29]([O:31][C:32](=[O:46])[CH2:33][CH2:34][CH2:35][C:36]([C:38]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:39]=1[O:45][CH2:2][C:3]([N:5]1[CH2:10][C@H:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:7][C@H:6]1[CH3:20])=[O:4])=[O:37])[CH3:30]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 219732762-Chloro-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanoneHCID 696556155-(5-Chloro-2-hydroxy-phenyl)-5-oxo-pentanoic acid ethyl ester

Product 1

HCID 696556725-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-5-oxo-pentanoic Acid Ethyl EsterYield 47.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2-chloro-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.10 g, 0.35 mmol) in 2-butanone (1 mL) was added potassium carbonate (0.13 g, 0.90 mmol), potassium iodide (0.065 g, 0.39 mmol) and 5-(5-chloro-2-hydroxy-phenyl)-5-oxo-pentanoic acid ethyl ester (0.11 g, 0.39 mmol). The reaction was stirred at 60° C. for 12 hours, then cooled and concentrated. Chromatography on silica gel gave the title compound (0.089 g).

Workup

  1. temperaturecooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-84897336acda45b98ea9115bb060396a
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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