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1-(2-Methoxyphenyl)piperazine → 2,3-dimethoxy-N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}benzamide

HRID 638160
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 638160
[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.[NH2:16][CH2:17][CH2:18]Br.C(N(CC)CC)C.[CH3:27][O:28][C:29]1[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32]>C(OCC)(=O)C.C(O)CCC>[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]([CH2:18][CH2:17][NH:16][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:29]=2[O:28][CH3:27])[CH2:11][CH2:10]1
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Komponenten

7

Edukt 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 8471TriethylamineHCID 27583922,3-Dimethoxybenzoyl chlorideHCID 27742172-Bromoethylamine hydrobromide

Produkt 1

HCID 133184852,3-dimethoxy-N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}benzamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 263
1-Butanol
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 1.92 g (0.01 mol) of 1-(2-methoxyphenyl)piperazine, 2,05 g (0.01 mol) of 2-aminoethylbromide hydrobromide, 2.5 g of triethylamine and 20 ml of n-butanol were added, and the mixture was refluxed for 6 hours. After the reaction, the mixture was concentrated under vacuum, and to the resulting residue, 2.5 g of anhydrous sodium carbonate, 20 ml of water and 20 ml of ethyl acetate were added. Under agitation with cooling on ice, a solution of 2.2 g (0.011 mol) of 2,3-dimethoxybenzoyl chloride in a small amount of ethyl acetate was added dropwise to the mixture. Thereafter, the mixture was stirred for 30 minutes under cooling with ice and extracted with ethyl acetate by agitation for 30 minutes at room temperature. The separated organic layer was washed with water, and 1N HCl was added until the pH became 3.0. The aqueous layer was separated, neutralized with sodium hydroxide and extracted with ethyl acetate. The resulting organic layer was washed with water, dried with Glauber's salt and concentrated under vacuum. The residue was subjected to column chromatography on silica gel (solvent: chloroform/methanol=100:1) to provide 1.99 g (yield: 50%) of 1-(2-methoxyphenyl)-4[2-(2,3-dimethoxybenzoyl)aminoethyl]piperazine. Recrystallization from isopropanol gave a colorless acicular crystal having a melting point of 133°-134° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 6 hours
  2. customAfter the reaction
  3. concentrationthe mixture was concentrated under vacuum
  4. additionto the resulting residue, 2.5 g of anhydrous sodium carbonate, 20 ml of water and 20 ml of ethyl acetate were added
  5. temperatureUnder agitation with cooling on ice
  6. temperatureunder cooling with ice
  7. extractionextracted with ethyl acetate by agitation for 30 minutes at room temperature
  8. washThe separated organic layer was washed with water, and 1N HCl
  9. additionwas added until the pH
  10. customThe aqueous layer was separated
  11. extractionextracted with ethyl acetate
  12. washThe resulting organic layer was washed with water
  13. dry with materialdried with Glauber's salt
  14. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9d63571007234cb9b1f2c224c304f6d2
Quelldatensatz
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04560686

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