1-(2-Methoxyphenyl)piperazine → 6-(2-[4-(2-Methoxyphenyl)-piperazin-1-yl]-ethyl)-benzoxazolinone

HRID 637702Notes

Reaction equation

HRID 637702 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.Br[CH2:16][CH2:17][C:18]1[CH:27]=[CH:26][C:21]2[NH:22][C:23](=[O:25])[O:24][C:20]=2[CH:19]=1>O1CCOCC1.[OH-].[Na+]>[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][N:12]([CH2:16][CH2:17][C:18]2[CH:27]=[CH:26][C:21]3[NH:22][C:23](=[O:25])[O:24][C:20]=3[CH:19]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 133060876-Bromoethylbenzoxazolone

Product 1

HCID 133435266-(2-[4-(2-Methoxyphenyl)-piperazin-1-yl]-ethyl)-benzoxazolinoneYield 66.5%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

0.025 mol (4.82 g) of 1-(2-methoxyphenyl)-piperazine and 0.02 mol (4.85 g) of 6-(2-bromoethyl)-benzoxazolinone, dissolved beforehand in 50 cm3 of dioxane, were introduced into a 100 cm3 flask with a ground glass neck, fitted with a reflux condenser, and the mixture was then heated under reflux for 72 hours, with stirring. After cooling, filtration and drying, the precipitate formed was dissolved in a sufficient amount of a 3% aqueous solution of sodium hydroxide. A stream of carbon dioxide was then bubbled and the precipitate was filtered off, washed and dried. Recrystallisation from toluene gave 4.7 g of the title product having a melting point of 182°-184° C.

Workup

  1. additionwere introduced into a 100 cm3 flask with a ground glass neck
  2. customfitted with a reflux condenser
  3. temperaturethe mixture was then heated
  4. temperatureunder reflux for 72 hours
  5. temperatureAfter cooling
  6. filtrationfiltration
  7. customdrying
  8. customthe precipitate formed
  9. customA stream of carbon dioxide was then bubbled
  10. filtrationthe precipitate was filtered off
  11. washwashed
  12. customdried
  13. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-1a910469e55e4faaad73c7dd64de4c82
Source dataset
uspto-grants-1985_12
Patent number
US04558060

Reaction notes

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