4-Bromo-2-methylbenzoic acid → (4-Bromo-2-methylphenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 2411249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2411249
[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[C:18]([CH3:25])[CH:17]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>C(Cl)(Cl)Cl.CO>[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:12]2[CH2:11][CH2:10][N:9]([C:3]3[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]=3)[CH2:14][CH2:13]2)=[O:21])=[C:18]([CH3:25])[CH:17]=1

Komponenten

6

Edukt 3

HCID 995704-Bromo-2-methylbenzoic acidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 584844961-(3,5-Dimethylpyridin-2-yl)piperazine

Produkt 1

HCID 58484835(4-Bromo-2-methylphenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanoneAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

1-(3,5-Dimethylpyridin-2-yl)piperazine (3.8 g) described in Preparation Example 79 and 4-bromo-2-methylbenzoic acid (4.3 g) were dissolved in a solution of chloroform (30 mL) and methanol (30 mL), 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (8.8 g) was added, and the mixture was stirred at room temperature overnight. The solvent was evaporated from the reaction mixture, ethyl acetate was added, and the insoluble material was collected by filtration. The solvent was evaporated from the obtained filtrate, and the residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (7 g).

Aufarbeitung

  1. additionwas added
  2. customThe solvent was evaporated from the reaction mixture, ethyl acetate
  3. additionwas added
  4. filtrationthe insoluble material was collected by filtration
  5. customThe solvent was evaporated from the obtained filtrate
  6. customthe residue was purified by column chromatography (hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0e0613eb7f1b41298e739ce964ce5c89
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08816079B2

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