Dimethyl Sulfoxide → 1-[5-(4-Methyl-pyrazol-1-yl)-2-nitro-phenyl]-piperidine

HRID 646875

Reaktionsgleichung

Reaktionsgleichung von HRID 646875
F[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1.C[C:18]1[CH:22]=[CH:21][NH:20][N:19]=1.[OH-].[Na+].[CH3:25]S(C)=O>CCOC(C)=O>[CH3:25][C:22]1[CH:18]=[N:19][N:20]([C:2]2[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[CH:7]=2)[CH:21]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 532567081-(5-Fluoro-2-nitrophenyl)piperidineHCID 178428694HCID 178428694, Verbindung

Produkt 1

HCID 686843421-[5-(4-Methyl-pyrazol-1-yl)-2-nitro-phenyl]-piperidineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1-(5-fluoro-2-nitro-phenyl)-piperidine (98 mg, 0.43 mmol, as prepared in Example 22, step (a), 3-methylpyrazole (49.2 mg, 0.6 mmol), and NaOH (22.4 mg, 0.56 mmol) were heated in 3 mL of DMSO at 90° C. overnight. The reaction was diluted with EtOAc (50 mL), washed with water (2×50 mL), dried (Na2SO4) and concentrated in vacuo to afford 117 mg (95%) the title compound as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C15H18N4O2 287.1 (M+H), found 287.1.

Aufarbeitung

  1. washwashed with water (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e73a654692564a71ae05df4223126f37
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705042B2

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