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1-(2-Methoxyphenyl)piperazine → HCID 19752298, Verbindung

HRID 1885310
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1885310
[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][N:9]=1)=[O:7].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN1CCCC1=O>[ClH:1].[ClH:1].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[S:10][N:9]=2)=[O:7])[CH2:27][CH2:26]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10332575HCID 10332575, Verbindung

Produkt 1

HCID 19752298HCID 19752298, VerbindungAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387
N-methyl-2-pyrrolidone
Lösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of N-(3-chloropropyl)-1,2-benzisothiazole-3-carboxamide (4.2 g), 1-(2-methoxyphenyl)piperazine (3.3 g), potassium carbonate (4.55 g), and sodium iodide (100 mg) in dry N-methylpyrrolidinone (150 ml) was heated to 180° C., with stirring, under nitrogen. After 24 hr, the reaction mixture was allowed to cool to room temperature and partitioned between ether/water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed on silica using ether as the eluent. The appropriate fractions were collected and evaporated. The residue was taken up in ether and hydrogen chloride in ether was added. Recrystallization of the precipitate from methanol/dichloromethane/ether provided 2.12 g (26.6%) of product, mp 191°-194° C.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. custompartitioned between ether/water
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was chromatographed on silica
  7. customThe appropriate fractions were collected
  8. customevaporated
  9. additionhydrogen chloride in ether was added
  10. customRecrystallization of the precipitate from methanol/dichloromethane/ether

Quellen und Nachweise

ORD-Eintrag
ord-b2ad1499fd6a4ebbaecf836c7adab0d9
Quelldatensatz
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05143923

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