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Imidazole → HCID 9907008, Verbindung

HRID 1645816
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1645816
Cl.O[CH:3]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[CH2:7][CH2:6]1.S(Cl)(Cl)=O.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>CCOCC.CO.O>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:8]1[CH2:9][CH2:10][N:5]([CH2:4][CH:3]([N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6][CH2:7]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 67749831HCID 67749831, Verbindung

Produkt 1

HCID 9907008HCID 9907008, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel
HCID 3283
Diethyl Ether
Lösungsmittel

Versuchsvorschrift

A mixture of 1-(2-hydroxy-2-phenylethyl)-4-(2-methoxyphenyl) piperazine hydrochloride (1.6 g) and thionyl chloride (5 ml) was stirred at reflux for 5 min. The clear solution was then diluted with ether and the precipitated product collected by filtration and washed well with ether. The solid was added to a solution of imidazole (2.4 g, 40 mmol) in methanol (20 ml) and heated to reflux for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed several times with water, dried (Na2SO4), and concentrated in vacuo. The residue was dissolved in ethanol (10 ml) and acidified with ethereal-HC1. Further addition of ether precipitated the hydrochloride (1.07 g, 55%), which was recrystallised from methanol-ethanol (20 ml; 1:3) to afford the title compound as the trihydrochloride 1.25 hydrate (0.54 g), m.p. 203°-204° C. (Found: C,53.2; H,6.4; N,11.2. C22H26N4O.3HC1.1.25 H2O requires C,53.4; H,6.4; N,11.3%).

Aufarbeitung

  1. temperatureat reflux for 5 min
  2. filtrationthe precipitated product collected by filtration
  3. washwashed well with ether
  4. temperatureheated
  5. temperatureto reflux for 1 h
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed several times with water
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. dissolutionThe residue was dissolved in ethanol (10 ml)
  11. additionFurther addition of ether
  12. customprecipitated the hydrochloride (1.07 g, 55%), which
  13. customwas recrystallised from methanol-ethanol (20 ml; 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-14d263ef60914b97ae1ef44620804cfc
Quelldatensatz
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05177078

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