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Acetone → 6-[2-(isopropylamino)ethyl]-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

HRID 1615027
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Reaktionsgleichung

Reaktionsgleichung von HRID 1615027
[NH2:1][CH2:2][CH2:3][N:4]1[C:16]2[CH:15]=[CH:14][C:13]3[C:17](=[O:20])[CH2:18][CH2:19][C:12]=3[C:11]=2[C:10]2[C:9]3[CH2:21][CH2:22][C:23](=[O:24])[C:8]=3[CH:7]=[CH:6][C:5]1=2.[CH3:25][C:26]([CH3:28])=O.C([O-])(O)=O.[Na+].Cl>C(Cl)Cl.CO.O1CCOCC1.C(Cl)(Cl)Cl.CO>[CH:26]([NH:1][CH2:2][CH2:3][N:4]1[C:16]2[CH:15]=[CH:14][C:13]3[C:17](=[O:20])[CH2:18][CH2:19][C:12]=3[C:11]=2[C:10]2[C:9]3[CH2:21][CH2:22][C:23](=[O:24])[C:8]=3[CH:7]=[CH:6][C:5]1=2)([CH3:28])[CH3:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 453811166-(2-aminoethyl)-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

Produkt 1

HCID 445191266-[2-(isopropylamino)ethyl]-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887
Methanol
Lösungsmittel
2×
HCID 6344DichloromethaneLösungsmittel3×
HCID 312751,4-DioxaneLösungsmittel
HCID 21584188Chloroform methanolLösungsmittel

Versuchsvorschrift

Crude compound 59 (1.69 g) was suspended in CH2Cl2 (200 mL). Then acetone (4 mL) and STAB (3.4 g) were added. The mixture was stirred for 24 h (TLC monitoring, eluent: CHCl3-MeOH, 9:1), then poured into an aqueous NaHCO3 solution. Then, another portion of CH2Cl2 and MeOH was added. The organic layer was separated, evaporated, washed with MeCN and ether. Yield of Example 8: 0.759 g. For the preparation of hydrochloride, the isolated product was suspended in a mixture of CH2Cl2 and MeOH, then a solution of HCl in dioxane was added. The resulting mixture was evaporated to dryness, and ethanol was added to the residue. The ethanolic solution was refluxed and cooled, and the precipitate was filtered. Yield of compound Example 8 hydrochloride: 0.684 g. 1H-NMR (DMSO-D6) spectrum: δ 1.24 (6H, d, J=6.6 Hz); 2.77-2.79 (4H, m); 3.34-3.43 (3H, m); 3.81-3.84 (4H, m); 4.91 (2H, t, J=7.3 Hz); 7.83 (2H, d, J=8.6 Hz); 7.91 (2H, d, J=8.6 Hz); 9.11 (2H, br. s). ELSD: 100%, ESI-MS: m/z 360 [M+H].+

Aufarbeitung

  1. customThe organic layer was separated
  2. customevaporated
  3. washwashed with MeCN and ether
  4. customFor the preparation of hydrochloride
  5. customThe resulting mixture was evaporated to dryness, and ethanol
  6. additionwas added to the residue
  7. temperatureThe ethanolic solution was refluxed
  8. temperaturecooled
  9. filtrationthe precipitate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-5bf5a18a85a948cdb93ff2eb37b576e7
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08765738B2

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