1-(2-Methoxyphenyl)piperazine → HCID 19066133, compound

HRID 481298Notes

Reaction equation

HRID 481298 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12]C)=[O:11])=[CH:5][CH:4]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C(N(CC)CC)C.O1CCOCC1>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[CH2:27][CH2:26][N:25]([CH2:2][C:3]2[CH:4]=[CH:5][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetate

Product 1

HCID 19066133HCID 19066133, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

In triethylamine (3 ml)-dioxane (80 ml) were dissolved 2.4 g of methyl 4-bromomethylphenylacetate and 1.9 g of 1-(2-methoxyphenyl)piperazine and the solution was stirred at room temperature for 4 hours. The solvent was then distilled off and the residue was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by column chromatography [silica gel, hexane-ethyl acetate=2:1] and the resulting oil was refluxed in a mixture of 30 ml 2N-sodium hydroxide and 10 ml methanol for 3 hours. The solvent was then distilled off and the residue was dissolved in water and filtered. The filtrate was neutralized with acetic acid and extracted with chloroform. The solvent was then distilled off and the residue was recrystallized from methanol-ethylether to provide 2.0 g of the title compound melting at 87° C.-90° C. The IR absorption spectrum of this product is presented in FIG. 2.

Workup

  1. distillationThe solvent was then distilled off
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography [silica gel, hexane-ethyl acetate=2:1]
  7. temperaturethe resulting oil was refluxed in a mixture of 30 ml 2N-sodium hydroxide and 10 ml methanol for 3 hours
  8. distillationThe solvent was then distilled off
  9. dissolutionthe residue was dissolved in water
  10. filtrationfiltered
  11. extractionextracted with chloroform
  12. distillationThe solvent was then distilled off
  13. customthe residue was recrystallized from methanol-ethylether

Sources & evidence

ORD record
ord-7068ff09609840faaed50264665fd0fc
Source dataset
uspto-grants-1998_08
Patent number
US05789409

Reaction notes

Loading…