1-(4-Fluorophenyl)piperazine → HCID 13343503, compound

HRID 637700Notes

Reaction equation

HRID 637700 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:14][N:15]1[C:19]2[CH:20]=[CH:21][C:22]([CH2:24][CH2:25]Br)=[CH:23][C:18]=2[O:17][C:16]1=[O:27]>O1CCOCC1>[CH3:14][N:15]1[C:19]2[CH:20]=[CH:21][C:22]([CH2:24][CH2:25][N:11]3[CH2:12][CH2:13][N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH2:9][CH2:10]3)=[CH:23][C:18]=2[O:17][C:16]1=[O:27]

Participants

4

Reactant 2

HCID 752601-(4-Fluorophenyl)piperazineHCID 13306088HCID 13306088, compound

Product 1

HCID 13343503HCID 13343503, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.025 mol (4.5 g) of 1-(4-fluorophenyl)-piperazine and 0.02 mol (5.12 g) of 3-methyl-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, 100 cm3 of a 3% strength aqueous solution of sodium hydroxide were added to the precipitate obtained, and the mixture was stirred for 30 minutes. Filtration, drying and recrystallisation from toluene gave 4.6 g of the title product having a melting point of 161°-164° 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. addition100 cm3 of a 3% strength aqueous solution of sodium hydroxide were added to the precipitate
  9. customobtained
  10. stirringthe mixture was stirred for 30 minutes
  11. filtrationFiltration
  12. customdrying
  13. customrecrystallisation from toluene

Sources & evidence

ORD record
ord-13958340b83541c7b412a670ccf402de
Source dataset
uspto-grants-1985_12
Patent number
US04558060

Reaction notes

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