Dichloromethane → N-(4-acetylamino-5-chloro-2-methoxyphenyl)-4-benzylpiperazine-1-carboxamide

HRID 1065230

Reaktionsgleichung

Reaktionsgleichung von HRID 1065230
[C:1]([NH:4][C:5]1[C:15]([Cl:16])=[CH:14][C:8](C(N=[N+]=[N-])=O)=[C:7]([O:17][CH3:18])[CH:6]=1)(=[O:3])[CH3:2].ClCCl.[CH2:22]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[N-:35]=[C:36]=[O:37]>C1(C)C=CC=CC=1>[C:1]([NH:4][C:5]1[C:15]([Cl:16])=[CH:14][C:8]([NH:35][C:36]([N:32]2[CH2:33][CH2:34][N:29]([CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:30][CH2:31]2)=[O:37])=[C:7]([O:17][CH3:18])[CH:6]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 759941-BenzylpiperazineHCID 105034IsocyanateHCID 205387424-Acetylamino-5-chloro-2-methoxy-benzoyl azide

Produkt 1

HCID 20538750N-(4-acetylamino-5-chloro-2-methoxyphenyl)-4-benzylpiperazine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of the 4-acetylamino-5-chloro-2-methoxy benzoyl azide (e7) (1.35 g) in dry toluene (30 ml) was heated to 90° for 30 minutes with stirring under dry nitrogen until the evolution of nitrogen ceased. A dichloromethane solution of 1-benzylpiperazine (0.9 g) was then added to the cooled suspension of the isocyanate (e8) and the resulting solution stirred at room temperature for 1 hour. The reaction mixture was then poured into petrol (200 ml) and the precipitated solid filtered off. Recrystallisation from toluene gave the N-(4-acetylamino-5-chloro-2-methoxyphenyl)-4-benzylpiperazine-1-carboxamide (e9) (1.4 g) m.p. 174°.

Aufarbeitung

  1. stirringthe resulting solution stirred at room temperature for 1 hour
  2. filtrationthe precipitated solid filtered off
  3. customRecrystallisation from toluene

Quellen und Nachweise

ORD-Eintrag
ord-4652f141642549e89e5eda7c739dbfaa
Quelldatensatz
uspto-grants-1982_05
Patentnummer
US04329344

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