1-(2-Methoxyphenyl)piperazine → HCID 10181699, compound

HRID 1066059Notes

Reaction equation

HRID 1066059 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]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=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]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=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 21197963HCID 21197963, compound

Product 1

HCID 10181699HCID 10181699, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension containing 2-methoxyphenylpiperazine (1.0 mmole), potassium carbonate (2.0 mmole), potassium iodide (0.5 mmole) and 4-benzyl-5-chloromethyl-2-phenyloxazole (1.0 mmole) from example 6, was stirred in acetone (15 ml) at ambient temperature for 16 hr. The solvent was removed in vacuo, water (50 ml) added and the product extracted into ethyl acetate (2×50 ml). The combined organics were washed with water (40 ml), brine (40 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 (0.74 mmole, 74% yield). This was transformed into its mono-fumarate salt, an off-white crystalline powder, using the procedure outlined in example 10 above. mp 175-175° C.

Workup

  1. customThe solvent was removed in vacuo, water (50 ml)
  2. additionadded
  3. extractionthe product extracted into ethyl acetate (2×50 ml)
  4. washThe combined organics were washed with water (40 ml), brine (40 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-b64d6bc396aa49499bffb12c7dd250cb
Source dataset
uspto-grants-2001_06
Patent number
US06242448B1

Reaction notes

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