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

HRID 1253271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253271
[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[N:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH2:20][CH2:19]1.C1(C)C(C)=CC=CC=1>O>[N:25]1[CH:26]=[CH:27][CH:28]=[N:29][C:24]=1[N:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH2:15][CH2:14][N:13]2[C:7](=[O:9])[CH:6]3[C:2]([CH3:1])([CH3:12])[CH:3]([CH2:4][CH2:5]3)[C:10]2=[O:11])[CH2:19][CH2:20]1

Komponenten

5

Edukt 3

HCID 7237O-XyleneHCID 128407054-(2-Pyrimidinyl)-1-piperazinebutanamineHCID 197972038,8-Dimethyl-3-oxabicyclo(3.2.1)octane-2,4-dione

Produkt 1

HCID 140971643-[4-[4-(2-Pyrimidinyl)-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-(2-pyrimidinyl)piperazine (2.55 g., 11 mmole) were combined in 500 ml. of xylene and refluxed for 48 hours with water removal via a Dean-Stark trap. The solvent was removed in vacuo and the residue column chromatographed on 100 g. of silica gel using a gradient elution from straight chloroform to 5% ethanol/chloroform. Concentration of the product in vacuum and recrystallization from isopropanol with addition of 4N isopropanolic HCl and acetone gave 600 mg. of the title compound as the dihydrochloride, monohydrate; m.p. 227°-229° C. (d).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue column chromatographed on 100 g
  3. washof silica gel using a gradient elution from straight chloroform to 5% ethanol/chloroform
  4. customConcentration of the product in vacuum and recrystallization from isopropanol
  5. additionwith addition of 4N isopropanolic HCl and acetone
  6. customgave 600 mg

Quellen und Nachweise

ORD-Eintrag
ord-8ddbe2487e454406bb2cccb7cc2b861b
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04748240

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