Potassium Iodide → rel-Methyl 5-chloro-2-[2-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethyl-1-piperazinyl]-2-oxoethoxy]benzoate

HRID 480180Notes

Reaction equation

HRID 480180 reaction equation
Cl[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].[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([OH:32])=[C:26]([CH:31]=1)[C:27]([O:29][CH3:30])=[O:28].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC.C(OCC)(=O)C>[CH3:30][O:29][C:27](=[O:28])[C:26]1[CH:31]=[C:22]([Cl:21])[CH:23]=[CH:24][C:25]=1[O:32][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]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl esterHCID 113584612-Chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

Product 1

HCID 11487716rel-Methyl 5-chloro-2-[2-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethyl-1-piperazinyl]-2-oxoethoxy]benzoateYield 100%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R, 5S)-2-chloro-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone (2.75 g, 9.2 mmol) in butanone (50 ml) was added methyl 5-chloro-2-hydroxybenzoate (1.55 g, 9.2 mmol), potassium carbonate (2.54 g, 18.4 mmol) and potassium iodide (1.52 g, 9.2 mmol). The resulting mixture was stirred at reflux for 6 hours. The reaction was then cooled, diluted with ethyl acetate, and washed with brine. The organics were dried over magnesium sulfate, filtered and concentrated in vacuo to give an orange oil. Chromatography on silica gel gave the title compound (4.1 g, 100% yield).

Workup

  1. temperatureat reflux for 6 hours
  2. temperatureThe reaction was then cooled
  3. washwashed with brine
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give an orange oil

Sources & evidence

ORD record
ord-0bbd530cffe4437d9db6db0082936d76
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

Loading…