O-Xylene → 3-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-8,8-dimethyl-3-azabicyclo[3.2.1]octane-2,4-dione

HRID 1253270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253270
[CH3:1][C:2]1([CH3:12])[CH:6]2[C:7]([O:9][C:10](=[O:11])[CH:3]1[CH2:4][CH2:5]2)=O.[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[N:28][CH:27]=[C:26]([Cl:30])[N:25]=2)[CH2:20][CH2:19]1.C1(C)C(C)=CC=CC=1>O>[Cl:30][C:26]1[N:25]=[C:24]([N:21]2[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][CH2:15][CH2:14][N:13]3[C:7](=[O:9])[CH:6]4[C:2]([CH3:1])([CH3:12])[CH:3]([CH2:4][CH2:5]4)[C:10]3=[O:11])[CH2:23][CH2:22]2)[CH:29]=[N:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 7237O-XyleneHCID 140865264-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amineHCID 197972038,8-Dimethyl-3-oxabicyclo(3.2.1)octane-2,4-dione

Produkt 1

HCID 141563833-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-8,8-dimethyl-3-azabicyclo[3.2.1]octane-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2,2-Dimethylcyclopentane-1,3-dicarboxylic anhydride (1.68 g., 10 mmole) and 1-(4-aminobutyl)-4-(6-chloro-2-pyrazinyl)piperazine (2.97 g., 11 mmole) were combined in 500 ml. of xylene and refluxed for 48 hours with Dean-Stark water removal. Concentration in vacuum, column chromatography on 100 g. of silica gel with chloroform, and recrystallization from 50 ml. of isopropanol with addition of 4N isopropanolic HCl gave 0.55 g. of the title compound as the monohydrochloride; m.p. 210° C. (d).

Aufarbeitung

  1. concentrationConcentration in vacuum, column chromatography on 100 g
  2. customof silica gel with chloroform, and recrystallization from 50 ml
  3. additionof isopropanol with addition of 4N isopropanolic HCl
  4. customgave 0.55 g

Quellen und Nachweise

ORD-Eintrag
ord-759e9be378344115804eb0877f7c45f7
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04748240

Notizen zur Reaktion

Wird geladen…