Formaldehyde → Methyl 11-[2-(4-methylpiperazino)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

HRID 1885221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885221
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C=O.F[C:11](F)(F)C(O)=O.[CH2:17]=[C:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][O:21][C:20]2[CH:29]=[CH:30][C:31]([C:33]([O:35][CH3:36])=[O:34])=[CH:32][C:19]1=2>ClCC(Cl)(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:11][CH:17]=[C:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][O:21][C:20]3[CH:29]=[CH:30][C:31]([C:33]([O:35][CH3:36])=[O:34])=[CH:32][C:19]2=3)[CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 531671-MethylpiperazineHCID 10106958HCID 10106958, Verbindung

Produkt 1

HCID 53817464Methyl 11-[2-(4-methylpiperazino)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 124181,1,1,2-TetrachloroethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

4-Methylpiperazine, 30 ml, and 74 g of paraformaldehyde were dissolved in 2 l of tetrachloroethane and 100 ml of trifluoroacetic acid was dropwise added to the solution. After stirring at 60° C. for 2 hours, a solution of 36 g of methyl 11-methylene-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate in 600 ml of tetrachloroethane was dropwise added to the reaction mixture followed by stirring at 90° C. for further 3 hours. The reaction mixture was concentrated to dryness under reduced pressure and 4 N hydrochloric acid aqueous solution was added to the residue to adjust pH to 1. Then, the mixture was washed with diethyl ether. Thereafter, 10 N sodium hydroxide aqueous solution was added to adjust pH to 13. Extraction was performed with 3 (of methylene chloride. After washing with saturated sodium chloride aqueous solution and drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate:triethylamine=5:5:1) to give 44 g of methyl 11-[2-(4-methyl-1-piperazinyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate as colorless oil.

Aufarbeitung

  1. stirringby stirring at 90° C. for further 3 hours
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure and 4 N hydrochloric acid aqueous solution
  3. additionwas added to the residue
  4. washThen, the mixture was washed with diethyl ether
  5. additionThereafter, 10 N sodium hydroxide aqueous solution was added
  6. extractionExtraction
  7. washAfter washing with saturated sodium chloride aqueous solution
  8. dry with materialdrying over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1aa2ec7ddccc4a1cbcc93cd1762417c6
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05143922

Notizen zur Reaktion

Wird geladen…