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Potassium Carbonate → 1-(1-Cyclopropylpiperazin-4-yl)-3-(4-methoxyphenyl)isoquinoline dihydrochloride

HRID 1251153
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1251153
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:3]=1.[ClH:20].[CH:21]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[ClH:1].[ClH:20].[CH:21]1([N:24]2[CH2:29][CH2:28][N:27]([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=[C:4]([C:12]4[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=4)[N:3]=3)[CH2:26][CH2:25]2)[CH2:23][CH2:22]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 225026591-Chloro-3-(4-methoxyphenyl)isoquinolineHCID 225027521-Cyclopropylpiperazine hydrochloride

Produkt 1

HCID 226712261-(1-Cyclopropylpiperazin-4-yl)-3-(4-methoxyphenyl)isoquinoline dihydrochlorideAusbeute 16,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1-Chloro-3-(4-methoxyphenyl)isoquinoline (514 mg), and 1-cyclopropylpiperazine hydrochloride salt (378 mg) described in JP-A 62-129273 were dissolved in dimethyl sulfoxide (7 ml), followed by the addition of potassium carbonate (788 mg), and the resulting mixture was stirred at 100° C. overnight. The reaction mixture was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system). The resulting product was converted into a hydrochloride in a conventional manner, and then recrystallized from ethanol/isopropyl ether, to give the hydrochloride of the title compound as yellow crystals (136 mg, yield; 16%).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe resulting organic layer was washed with water
  3. dry with materialdried (over MgSO4)
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)
  6. customrecrystallized from ethanol/isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ee611fe8dbcd4e35bf86c12f49f00bb1
Quelldatensatz
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06340759B1

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