Tacrine → 1,2,3,4-Tetrahydroacridine

HRID 2356999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356999
[CH:1]1[CH:2]=[CH:3][C:4]2[C:5](=[C:7](N)[C:8]3[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=3[N:10]=2)[CH:6]=1.BrCCCC(Cl)=O>C(Cl)(Cl)Cl.CN(C)C=O>[CH2:14]1[C:8]2[C:9](=[N:10][C:4]3[C:5]([CH:7]=2)=[CH:6][CH:1]=[CH:2][CH:3]=3)[CH2:11][CH2:12][CH2:13]1

Komponenten

5

Edukt 2

HCID 1935TacrineHCID 702254-Bromobutyryl chloride

Produkt 1

HCID 1553151,2,3,4-Tetrahydroacridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of tacrine (4 g, 20.17 mmoles) in chloroform (50 ml) and N,N-dimethylformamide (15 ml), 4-bromobutyroylchloride (3.5 ml, 30.25 mmoles) is added. The reaction mixture is maintained under stirring at room temperature for 6 hours and then diluted with chloroform and washed with water. The organic phase, anhydrified with sodium sulphate, is evaporated at reduced pressure. The crude product is purged by chromatography on silica gel, eluting with n-hexane/ethyl acetate 8/2 (ratio by volume). 9-[4-bromo)butyroylamino]-1,2,3,4-tetrahydroacridine is obtained.

Aufarbeitung

  1. temperatureThe reaction mixture is maintained
  2. washwashed with water
  3. customis evaporated at reduced pressure
  4. customThe crude product is purged by chromatography on silica gel
  5. washeluting with n-hexane/ethyl acetate 8/2 (ratio by volume)

Quellen und Nachweise

ORD-Eintrag
ord-387aecefefb645d799e484305ffda361
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759392B2

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