Potassium Hydroxide → HCID 11223585, Verbindung

HRID 1821092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821092
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][CH:17]=1)[C:14]([NH2:18])=[C:13]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)=[N:7]2.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br>CS(C)=O>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:18][C:14]1[C:15]2[C:6]([N:7]=[C:8]3[C:13]=1[CH2:12][CH2:11][CH2:10][CH2:9]3)=[CH:5][C:4]([Cl:3])=[CH:17][CH:16]=2

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 783091,7-DibromoheptaneHCID 103990689-AMINO-6-CHLORO-1,2,3,4-TETRAHYDRO-ACRIDINE

Produkt 1

HCID 11223585HCID 11223585, VerbindungAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Potassium hydroxide (95 mg, 1.7 mmoL) was added to a solution of 6-chloro-1,2,3,4-tetrahydro-acridin-9-ylamine (395 mg, 1.7 mmoL) in dimethylsulfoxide (15 ml) and the mixture was stirred vigorously under nitrogen at room temperature for 2 h. 1,7-Dibromoheptane (438 mg, 1.7 mmoL) was added, and the reaction was continued to stir at room temperature for 12 h. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The combined ethyl acetate extract was dried, filtered and concentrated. The resulting residue was purified by column chromatography on silica gel using hexane/ethyl acetate/triethyl amine (8/2/1) to provide the desired product (244 mg, 0.60 mmoL) in 35% yield.

Aufarbeitung

  1. stirringto stir at room temperature for 12 h
  2. extractionextracted with ethyl acetate
  3. extractionThe combined ethyl acetate extract
  4. customwas dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7fc91e80b31146e8814f7593282966bb
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07605265B2

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