1-Methyl-4-{2-[3-(methyloxy)-4-nitrophenyl]ethyl}piperazine → 2-Methoxy-4-[2-(4-methylpiperazin-1-yl)ethyl]aniline

HRID 419462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419462
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([O:19][CH3:20])[CH:11]=2)[CH2:4][CH2:3]1>CCOC(C)=O.CO>[CH3:20][O:19][C:12]1[CH:11]=[C:10]([CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:15]=[CH:14][C:13]=1[NH2:16]

Komponenten

3

Edukt 1

HCID 594526681-Methyl-4-{2-[3-(methyloxy)-4-nitrophenyl]ethyl}piperazine

Produkt 1

HCID 574161632-Methoxy-4-[2-(4-methylpiperazin-1-yl)ethyl]anilineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

1-Methyl-4-{2-[3-(methyloxy)-4-nitrophenyl]ethyl}piperazine (0.6 g, 2.15 mmol) was placed in a 100 mL high pressure vessel and dissolved in 30 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/carbon (0.42 g, 0.107 mmol) was added followed quickly by a rubber septum. The flask was evacuated and filled with N2 six times to remove any oxygen. The vessel was then pressurized with H2 (50 psi). The solution stirred overnight. The next morning the vessel was evacuated and filled with N2 six times to remove any H2. The solution was filtered through celite and evaporated to afford the title compound of step D (0.460 g, 1.84 mmol, 86%). 1H NMR (400 MHz, CDCl3) δ ppm 6.60-6.64 (m, 3H), 3.82 (s, 3H), 3.64 (bs, 2H), 2.64-2.73 (m, 2H), 2.38-2.63 (m, 10H), 2.29 (s, 3H).

Aufarbeitung

  1. customThe flask was evacuated
  2. additionfilled with N2 six times
  3. customto remove any oxygen
  4. customThe next morning the vessel was evacuated
  5. additionfilled with N2 six times
  6. customto remove any H2
  7. filtrationThe solution was filtered through celite
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b5b519374f5245b2b8384b78c3629d47
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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