Water → [5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-isoxazol-3-yl]-(4-methyl-piperazin-1-yl)-methanone

HRID 389935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389935
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8]([O:15][C:16]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([Cl:30])=[CH:18][C:17]=1[C:31]1[O:35][N:34]=[C:33]([C:36]([O:38]CC)=O)[CH:32]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.CCOC(C)=O>CCO>[CH2:8]([O:15][C:16]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([Cl:30])=[CH:18][C:17]=1[C:31]1[O:35][N:34]=[C:33]([C:36]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:38])[CH:32]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 531671-MethylpiperazineHCID 24774040Ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylate

Produkt 1

HCID 67083255[5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-isoxazol-3-yl]-(4-methyl-piperazin-1-yl)-methanoneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

N-methylpiperazine (25.4 mmol) was added to a suspension of ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylate (2.1 mmol) in EtOH (5 ml) and the reaction mixture was heated to 90° C. under stirring for 18 h. The reaction mixture was poured into a mixture of water (15 ml) and AcOEt (30 ml). After standard extraction, the organic layer was washed with water and brine, dried over Na2SO4, and evaporated. The resulting solid was purified by silica gel column chromatography (CHCl3/MeOH: 95/0.5) to give the desired compound (620 mg, 57%).

Aufarbeitung

  1. extractionAfter standard extraction
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe resulting solid was purified by silica gel column chromatography (CHCl3/MeOH: 95/0.5)

Quellen und Nachweise

ORD-Eintrag
ord-d02aaf6922c042feafff84b874da17c9
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383616B2

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