1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methyloxy)ethyl]piperazine → 5-Methyl-2-(methyloxy)-4-{4-[2-(methyloxy)ethyl]-1-piperazinyl}aniline

HRID 419658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419658
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][O:21][CH3:22])[CH2:15][CH2:14]1>CCOC(C)=O.CO>[CH3:1][C:2]1[C:3]([N:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][O:21][CH3:22])[CH2:17][CH2:18]2)=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:7]=1)[NH2:8]

Komponenten

3

Edukt 1

HCID 594526231-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methyloxy)ethyl]piperazine

Produkt 1

HCID 594528205-Methyl-2-(methyloxy)-4-{4-[2-(methyloxy)ethyl]-1-piperazinyl}anilineAusbeute 366,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methyloxy)ethyl]piperazine (1.44 g, 4.66 mmol) was placed in a 100 mL high pressure vessel and dissolved in 60 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/C (1.09 g, 0.28 mmol) was added followed quickly by a rubber septum. The vial was evacuated and filled with N2 six times to remove any oxygen. The vial was then pressurized with H2 (60 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 B (1.15 g, 17.07 mmol, 88%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.56 (s, 1H), 6.42 (s, 1H), 4.30 (s, 2H), 3.70 (s, 3H), 3.43 (t, J=5.87 Hz, 2H), 3.23 (s, 3H), 2.71 (t, J=4.58 Hz, 4H), 2.45-2.56 (m, 6H), 2.04 (s, 3H)

Aufarbeitung

  1. customThe vial 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-30a3fe884e1a4d7096e681d0cb83d62b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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