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Potassium Iodide → rel-1-(4-Fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]-1-butanone

HRID 1876771
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1876771
[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C@H:12]4[CH:17]=[N:16][CH2:15][CH2:14][C@@H:13]4[N:5]([C:6]=23)[CH2:4][CH2:3]1.Cl[CH2:19][CH2:20][CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:23].C(N(CC)CC)C.[I-].[K+]>O1CCOCC1.C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C@@H:12]4[CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]([C:24]5[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=5)=[O:23])[CH2:15][CH2:14][C@@H:13]4[N:5]([C:6]=23)[CH2:4][CH2:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 68591394HCID 68591394, Verbindung

Produkt 1

HCID 21302490rel-1-(4-Fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]-1-butanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A suspension of (6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido-[3′,4′:4,5]-pyrrolo[1,2,3-de]quinoxaline (ca. 11.8 g, ca. 50 mmol), 4-chloro-4′-fluorobutyrophenone (15.0 g, 74.8 mmol), triethylamine (30 mL, 214 mmol), and potassium iodide (12.6 g, 76 mmol) in dioxane (65 ml) and toluene (65 ml) is heated to reflux for 7 hours. After filtration and evaporation of the solvent, 200 ml of DCM is added. The DCM solution is washed with brine, dried (Na2SO4) and concentrated to approximately 55 ml. The concentrated solution is added dropwise to 600 ml of 0.5N HCl ether solution. The solid is filtered off and washed with ether and then dissolved in water. The resulting aqueous solution is basified with 2N NaOH and extracted with DCM. The DCM layers are combined, washed with brine (2×200 mL) and dried (Na2SO4). Evaporation of the solvent and chromatography of the residue over silica gel gives 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido-[3′,4′:4,5]-pyrrolo[1,2,3-de]quinoxalin-8-(7H)-yl)-1-(4-fluorophenyl)-1-butanone.

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux for 7 hours
  3. filtrationAfter filtration and evaporation of the solvent, 200 ml of DCM
  4. additionis added
  5. washThe DCM solution is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to approximately 55 ml
  8. additionThe concentrated solution is added dropwise to 600 ml of 0.5N HCl ether solution
  9. filtrationThe solid is filtered off
  10. washwashed with ether
  11. dissolutiondissolved in water
  12. extractionextracted with DCM
  13. washwashed with brine (2×200 mL)
  14. dry with materialdried (Na2SO4)
  15. customEvaporation of the solvent and chromatography of the residue over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ba15f9a6669b4bbcbbe677db18b01d27
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08309722B2

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