1-Methyl-4-(4-nitro-3-(piperidin-1-yl)phenyl)piperazine → 4-(4-Methylpiperazin-1-yl)-2-(piperidin-1-yl)aniline

HRID 646889

Reaktionsgleichung

Reaktionsgleichung von HRID 646889
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)[CH2:6][CH2:7]1

Komponenten

4

Edukt 1

HCID 28857041-Methyl-4-(4-nitro-3-(piperidin-1-yl)phenyl)piperazine

Produkt 1

HCID 686796964-(4-Methylpiperazin-1-yl)-2-(piperidin-1-yl)anilineAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

1-(5-Fluoro-2-nitro-phenyl)-piperidine (100 mg, 0.44 mmol) was treated with N-methylpiperizine (3 mL) and heated to 80° C. overnight. The reaction was diluted with EtOAc (10 mL), washed with water (2×10 mL), dried (Na2SO4) and concentrated in vacuo to afford 118 mg (88%) of 1-methyl-4-(4-nitro-3-piperidin-1-yl-phenyl)-piperazine as an oil. The 1-methyl-4-(4-nitro-3-piperidin-1-yl-phenyl)-piperazine (22 mg, 0.07 mmol) was stirred with 13 mg 5% Pd—C in 1 mL of MeOH under H2 for 2 h. The mixture was filtered through SiO2, eluting with 10% MeOH—CHCl3, and the solvent was concentrated in vacuo to give 17 mg (86%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C16H26N4, 275.22 (M+H), found 275.2.

Aufarbeitung

  1. filtrationThe mixture was filtered through SiO2
  2. washeluting with 10% MeOH—CHCl3
  3. concentrationthe solvent was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5e116b00b61b4ce28e5987071748db15
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705042B2

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