Potassium Iodide → HCID 21197966, compound

HRID 1066060Notes

Reaction equation

HRID 1066060 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:22]([C:29]1[N:30]=[C:31]([CH2:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[O:32][C:33]=1[CH2:34]Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC(C)=O>[CH2:22]([C:29]1[N:30]=[C:31]([CH2:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[O:32][C:33]=1[CH2:34][N:11]1[CH2:12][CH2:13][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:9][CH2:10]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 705291-(2-Fluorophenyl)piperazineHCID 21197964HCID 21197964, compound

Product 1

HCID 21197966HCID 21197966, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension containing 2-fluorophenylpiperazine (2.0 mmole), potassium carbonate (4.0 mmole), potassium iodide (1.0 mmole) and 4-benzyl-5-chloromethyl-2-cyclohexylmethyl oxazole (2.0 mmole) from example 8, was stirred in acetone (20 ml) at ambient temperature for 18 hr. The solvent was removed in vacuo, water (50 ml) added and the product extracted into ethyl acetate (3×50 ml). The combined organics were washed with water (50 ml), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The product was purified by “flash” chromatography over silica gel to afford the titled compound as an off-white crystalline powder (1.3 mmole, 65% yield). An ethyl acetate solution (10 ml) of the product was treated with 2 equivalents of ethereal 1N-HC1 to afford the HCl salt of the titled compound as a white solid.

Workup

  1. customThe solvent was removed in vacuo, water (50 ml)
  2. additionadded
  3. extractionthe product extracted into ethyl acetate (3×50 ml)
  4. washThe combined organics were washed with water (50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by “flash” chromatography over silica gel

Sources & evidence

ORD record
ord-0681d19415f549ca820e0d5e3a822a03
Source dataset
uspto-grants-2001_06
Patent number
US06242448B1

Reaction notes

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