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Hydrochloric Acid → N-(2-diethylaminoethyl)-4-(1,4-dihydroindeno[1,2-c]-pyrazol-3-yl)-benzamide dihydrochloride

HRID 990999
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 990999
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=O)=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[CH2:23]([N:25]([CH2:29][CH3:30])[CH2:26][CH2:27][NH2:28])[CH3:24].[ClH:31]>ClCCl.C(O)C>[ClH:31].[ClH:31].[CH2:23]([N:25]([CH2:29][CH3:30])[CH2:26][CH2:27][NH:28][C:17](=[O:19])[C:16]1[CH:21]=[CH:22][C:13]([C:3]2[C:4]3[CH2:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[NH:1][N:2]=2)=[CH:14][CH:15]=1)[CH3:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 60993N,N-DiethylethylenediamineHCID 18415839Methyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate

Produkt 1

HCID 18416003N-(2-diethylaminoethyl)-4-(1,4-dihydroindeno[1,2-c]-pyrazol-3-yl)-benzamide dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A mixture of methyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzoate (2.2 g, Example 7) and N,N-diethylethylenediamine (7 ml) was boiled under reflux for 5 hours. The mixture was cooled and stood for 16 hours at ambient temperature. Petroleum ether, b.p. 60-80° C. (50 ml) was added and then decanted off to leave a gum which was further treated with petroleum ether as above and the residual gum dissolved in dichloromethane and purified by flash column chromatography on silica using dichloromethane/IMS/triethylamine (25:2:1) as the mobile phase to give a solid which was dissolved in ethanol (70 ml) and then dry hydrogen chloride gas was passed through the solution. The precipated solid was collected by filtration, washed with ethanol and dried to give N-(2-diethylaminoethyl)-4-(1,4-dihydroindeno[1,2-c]-pyrazol-3-yl)- benzamide dihydrochloride, m.p.230° C.

Aufarbeitung

  1. temperatureunder reflux for 5 hours
  2. temperatureThe mixture was cooled
  3. customdecanted off
  4. customto leave a gum which
  5. custompurified by flash column chromatography on silica
  6. customto give a solid which
  7. filtrationThe precipated solid was collected by filtration
  8. washwashed with ethanol
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4b4165ae7d94484ba93cfa00b102bb0a
Quelldatensatz
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06462036B1

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