Potassium Iodide → 2-(4-chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone

HRID 11626

Reaction equation

HRID 11626 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:7][C@H:6]1[CH3:19])=[O:4].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:2][C:3]([N:5]2[CH2:10][CH2:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH2:7][C@H:6]2[CH3:19])=[O:4])=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 69804-Chloro-2-nitrophenolHCID 11430Potassium CarbonateHCID 600606302-Chloro-1-{(2R)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl}ethan-1-one

Product 1

HCID 600606312-(4-chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanoneYield 94.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 2-chloro-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone (0.40 g, 1.4 mmol) in 2-butanone (14 mL) was added 4-chloro-2-nitro-phenol (0.25 g, 1.4 mmol), potassium carbonate (0.39 g, 2.8 mmol) and potassium iodide (233 mg, 1.4 mmol). The reaction was refluxed overnight, cooled and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.56 g).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. temperaturecooled
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12b92824c8e24178912e292742904661
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

Loading…