1-(2-Methoxyphenyl)piperazine → HCID 13318464, compound

HRID 638159Notes

Reaction equation

HRID 638159 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(N(CC)CC)C.Br[CH2:23][CH2:24][NH:25][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1>[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]([CH2:23][CH2:24][NH:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 8471TriethylamineHCID 250996n-(2-bromo-ethyl)-benzamide

Product 1

HCID 13318464HCID 13318464, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 1.92 g (0.01 mol) of 1-(2-methoxyphenyl)piperazine, 1.01 g (0.01 mol) of triethylamine, 150 ml of toluene and 2.28 g (0.01 mol) of N-(2-bromoethyl)benzamide were added, and the mixture was refluxed for 3-4 hours under stirring. After the reaction, the solvent was concentrated under vacuum to half of its original volume, and a mixture of the residue with water was extracted with ethyl acetate. After separating the solvent layer, the aqueous layer was further extracted with ethyl acetate, and a mixture of the extract with the previously separated solvent layer was washed with water. To the organic layer, 1N HCl was added until the pH became 3.0, and the aqueous layer was separated. The separated aqueous layer was neutralized with aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried with Glauber's salt, and distilled under vacuum to remove the solvent. The resulting residue was mixed with benzene-ether to provide 2.03 g (yield: 60%) of crystalline 1-(2-methoxyphenyl)-4-(2-benzoylaminoethyl)piperazine. Recrystallization from a mixture of isopropyl alcohol and ether gave a colorless needles having a melting point of 139°-140° C.

Workup

  1. temperaturethe mixture was refluxed for 3-4 hours
  2. customAfter the reaction
  3. concentrationthe solvent was concentrated under vacuum to half of its original volume
  4. additiona mixture of the residue with water
  5. extractionwas extracted with ethyl acetate
  6. customAfter separating the solvent layer
  7. extractionthe aqueous layer was further extracted with ethyl acetate
  8. additiona mixture of the
  9. extractionextract with the previously separated solvent layer
  10. washwas washed with water
  11. additionTo the organic layer, 1N HCl was added until the pH
  12. customthe aqueous layer was separated
  13. extractionextracted with ethyl acetate
  14. washThe organic layer was washed with water
  15. dry with materiala saturated aqueous solution of sodium chloride, dried with Glauber's salt
  16. distillationdistilled under vacuum
  17. customto remove the solvent
  18. additionThe resulting residue was mixed with benzene-ether

Sources & evidence

ORD record
ord-ce642c2e7c15480cb61f64e32ad75b49
Source dataset
uspto-grants-1985_12
Patent number
US04560686

Reaction notes

Loading…