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Hydrochloric Acid → 8,9-dihydro-7-[(hydroxy)(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one hydrochloride

HRID 486192
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 486192
[OH:1][CH:2]([C:17]1[N:18]=[CH:19][N:20](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:21]=1[CH3:22])[CH:3]1[C:15](=[O:16])[N:7]2[C:8]3[C:13]([CH:14]=[C:6]2[CH2:5][CH2:4]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[ClH:42]>C(O)(=O)C.O.C(OCC)(=O)C.CCOCC>[ClH:42].[OH:1][CH:2]([C:17]1[N:18]=[CH:19][NH:20][C:21]=1[CH3:22])[CH:3]1[C:15](=[O:16])[N:7]2[C:8]3[C:13]([CH:14]=[C:6]2[CH2:5][CH2:4]1)=[CH:12][CH:11]=[CH:10][CH:9]=3
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Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 117569938,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one

Produkt 1

HCID 190973268,9-dihydro-7-[(hydroxy)(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel
HCID 21899381Acetic acid--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of 8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (1.1 g) in acetic acid-water (3:1, 48 ml) was stirred at 65° C. for 90 minutes. After evaporation of the solvent, the residue was diluted with water, neutralized with an aqueous solution of sodium hydrogencarbonate, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The obtained amorphous powder contained two products which showed close Rf values (0.3 and 0.4 respectively) by TLC (20% methanol-chloroform). Separation with silica gel column chromatography (10% methanol-chloroform) gave two fractions. The residue obtained from the first eluted fraction was dissolved in ethyl acetate and treated with hydrogen chloride in ether to give one isomer with an upper Rf value of 8,9-dihydro-7-[(hydroxy)(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one hydrochloride (86.1 mg), which was designated as the isomer A.

Aufarbeitung

  1. customAfter evaporation of the solvent
  2. additionthe residue was diluted with water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customshowed close Rf values (0.3 and 0.4 respectively) by TLC (20% methanol-chloroform)
  8. customSeparation with silica gel column chromatography (10% methanol-chloroform)
  9. customgave two fractions
  10. customThe residue obtained from the first eluted fraction

Quellen und Nachweise

ORD-Eintrag
ord-a7ed3fcc6b6b411dbb50f9ef97dab2e2
Quelldatensatz
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05290785

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