1-(4-Methoxy-2-nitrobenzyl)-4-methylpiperazine → 5-Methoxy-2-[(4-methylpiperazin-1-yl)methyl]aniline

HRID 1914678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914678
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[C:5]([N+:17]([O-])=O)[CH:4]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[C:5]([CH:4]=1)[NH2:17]

Komponenten

5

Edukt 2

HCID 593530491-(4-Methoxy-2-nitrobenzyl)-4-methylpiperazineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 593530635-Methoxy-2-[(4-methylpiperazin-1-yl)methyl]anilineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-methoxy-2-nitrobenzyl)-4-methylpiperazine (6 g; 25.5 mmol; 1 eq) in methanol (100 mL) was added palladium on charcoal (0.6 g; 10%) and the mixture is hydrogenated under atmospheric pressure of hydrogen for 3 h. The catalyst is filtered off and the filtrate is evaporated under vacuum. The crude residue is purified via column chromatography (eluent chloroform/methanol [9/1]) to afford 4.5 g (84%) of the title compound as a viscous liquid. 1H NMR (CDCl3, 400 MHz) δ 6.90-6.88 (m, 1H), 6.24-6.22 (m, 2H), 5.32 (br s, 2H), 3.82 (s, 3H), 3.47 (s, 2H), 2.46-2.30 (m, 8H), 2.25 (s, 3H). HPLC (max plot) 99%. LC/MS(ES+): 236.0.

Aufarbeitung

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated under vacuum
  3. customThe crude residue is purified via column chromatography (eluent chloroform/methanol [9/1])

Quellen und Nachweise

ORD-Eintrag
ord-a422f0b7101f4208818b224c592294f1
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614215B2

Notizen zur Reaktion

Wird geladen…