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Triethylamine → t-butyl 4-(5H-dibenzo[a,d][7]annulen-5-yl)-1-piperazine carboxylate

HRID 2061251
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2061251
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6](O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[N:28]1([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C1C=CC=CC=1.N1C=CC=CC=1>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([N:31]3[CH2:30][CH2:29][N:28]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 82577DibenzosuberenolHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 68420841t-butyl 4-(5H-dibenzo[a,d][7]annulen-5-yl)-1-piperazine carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241
Benzene
Lösungsmittel
HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

750 mg (3.60 mmol) of the compound obtained in step 1 described above was dissolved in 8 ml of benzene. 0.02 ml of pyridine was added to the obtained solution, and 3.5 ml (48.2 mmol) of thionyl chloride was added to the obtained mixture under cooling with ice. After stirring the reaction mixture at 0° C. for 1 hour and then at room temperature for 2 hours, the solvent was evaporated under reduced pressure. 10 ml of tetrahydrofuran was added to the residue. 2.5 ml (18 mmol) of triethylamine and 805 mg (4.32 mmol) of t-butyl piperazinecarboxylate were added to reaction mixture under cooling with ice. The temperature of the mixture was slowly elevated to room temperature, and it was stirred overnight. The solvent was evaporated under reduced pressure. Dichloromethane was added to the residue. After washing with water and saturated aqueous sodium chloride solution, the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduce pressure, and the residue was purified by the basic silica gel chromatography (hexane:dichloromethane=9:1) to obtain the title compound.

Aufarbeitung

  1. additionwas added to the obtained mixture
  2. temperatureunder cooling with ice
  3. waitat room temperature for 2 hours
  4. customthe solvent was evaporated under reduced pressure
  5. addition10 ml of tetrahydrofuran was added to the residue
  6. temperatureunder cooling with ice
  7. customwas slowly elevated to room temperature
  8. stirringit was stirred overnight
  9. customThe solvent was evaporated under reduced pressure
  10. additionDichloromethane was added to the residue
  11. washAfter washing with water and saturated aqueous sodium chloride solution
  12. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated
  14. customthe residue was purified by the basic silica gel chromatography (hexane:dichloromethane=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-51cc2934875b4ef6aa821feb423b44a7
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08278329B2

Notizen zur Reaktion

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