Dichloromethane → HCID 14156369, Verbindung

HRID 1253264

Reaktionsgleichung

Reaktionsgleichung von HRID 1253264
[CH:1]12[C:9](=[O:10])[O:8][C:6](=O)[CH:3]([CH2:4][CH2:5]1)[CH2:2]2.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[CH2:18][CH2:17]1.C(Cl)Cl.C1(C)C(C)=CC=CC=1>O>[Cl:28][C:24]1[CH:23]=[C:22]([N:19]2[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][CH2:13][CH2:12][N:11]3[C:6](=[O:8])[CH:3]4[CH2:2][CH:1]([CH2:5][CH2:4]4)[C:9]3=[O:10])[CH2:21][CH2:20]2)[CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 7237O-XyleneHCID 2397991,3-Cyclopentanedicarboxylic anhydrideHCID 128407044-[4-(3-Chlorophenyl)piperazin-1-yl]butan-1-amine

Produkt 1

HCID 14156369HCID 14156369, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1,3-Cyclopentane dicarboxylic anhydride (2.2 g., 15 mmole) and 4.0 g. (15 mmole) of 1-(4-aminobutyl)-4-(3-chlorophenyl)piperazine were combined in 300 ml. of methylene chloride and stirred for 30 minutes at room temperature. The solvent was replaced with xylene and the mixture was refluxed for 48 hours with water removal via a Dean-Stark trap. The solvent was removed in vacuum and the residue filtered through 75 g. of silica gel with 2% ethanol/chloroform as eluent. The product was concentrated in vacuum and crystallized from 50 ml. of isopropanol with addition of 4N isopropanolic HCl. Recrystallization from ethanol gave 1.6 g. of the title compound as the hydrochloride, quarter hydrate; m.p. 199°-202° C.

Aufarbeitung

  1. customThe solvent was removed in vacuum
  2. filtrationthe residue filtered through 75 g
  3. concentrationThe product was concentrated in vacuum
  4. customcrystallized from 50 ml
  5. additionof isopropanol with addition of 4N isopropanolic HCl
  6. customRecrystallization from ethanol
  7. customgave 1.6 g

Quellen und Nachweise

ORD-Eintrag
ord-0414f49d39d6428e8394f535d7f0ce73
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04748240

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