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1-Piperazinecarboxaldehyde → HCID 19421679, Verbindung

HRID 744088
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 744088
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)=[CH:35]C(O)=O)=[CH:30][CH:29]=1.C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.C(Cl)Cl>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([C:34]([C:31]2[CH:30]=[CH:29][C:28]([O:27][CH3:26])=[CH:33][CH:32]=2)=[CH:35][C:18]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])=[CH:44][CH:43]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 821911-PiperazinecarboxaldehydeHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 12660800HCID 12660800, Verbindung

Produkt 1

HCID 19421679HCID 19421679, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

3.41 ml of diphenylphosphoryl azide and 1.09 ml of 1-formylpiperazine were added to a 60 ml of a methylene chloride solution of 3.00 g of 3,3-bis(4-methoxyphenyl)acrylic acid and 2.94 ml of triethylamine. The reaction mixture was then stirred for 2 hours at room temperature, after which it was poured into a saturated aqueous solution of sodium bicarbonate and extracted twice with methylene chloride. The combined extracts were washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was dissolved in 80 ml of methanol, and 40 ml of a 10% w/v aqueous solution of sodium hydroxide were added to the resulting solution. The reaction mixture was stirred for 18 hours at room temperature and then poured into water; it was then extracted twice with methylene chloride. The combined extracts were washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography through 80 g of silica gel eluted with mixtures of methylene chloride and methanol ranging from 19:1 to 4:1 by volume to give 3.00 g of 1-[3,3-bis(4-methoxyphenyl)acryloyl]piperazine as a powder.

Aufarbeitung

  1. extractionextracted twice with methylene chloride
  2. washThe combined extracts were washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved in 80 ml of methanol
  6. addition40 ml of a 10% w/v aqueous solution of sodium hydroxide were added to the resulting solution
  7. stirringThe reaction mixture was stirred for 18 hours at room temperature
  8. additionpoured into water
  9. extractionit was then extracted twice with methylene chloride
  10. washThe combined extracts were washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. customevaporated under reduced pressure
  13. customThe residue was purified by column chromatography through 80 g of silica gel
  14. washeluted with mixtures of methylene chloride and methanol ranging from 19:1 to 4:1 by volume

Quellen und Nachweise

ORD-Eintrag
ord-cda698af916d453a83a4cef4817bb5b9
Quelldatensatz
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05559109

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