1-(2-Methoxyphenyl)piperazine → HCID 9955869, compound

HRID 1066058Notes

Reaction equation

HRID 1066058 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:23]([C:30]1[N:31]=[C:32]([CH2:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[O:33][C:34]=1[CH2:35]Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[CH2:23]([C:30]1[N:31]=[C:32]([CH2:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[O:33][C:34]=1[CH2:35][N:12]1[CH2:13][CH2:14][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:10][CH2:11]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 21197964HCID 21197964, compound

Product 1

HCID 9955869HCID 9955869, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension containing 2-methoxyphenylpiperazine (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 (1.62 mmole, 81% yield). This was transformed into its mono-fumarate salt, an off-white crystalline powder, using the procedure outlined in example 10 above.

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-423ccc81ed144ad498467f8f55f3f369
Source dataset
uspto-grants-2001_06
Patent number
US06242448B1

Reaction notes

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