HCID 59452727, Verbindung → HCID 59452788, Verbindung

HRID 419638

Reaktionsgleichung

Reaktionsgleichung von HRID 419638
[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]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]1>CCOC(C)=O.CO.C(Cl)Cl>[CH3:1][C:2]1[C:3]([N:13]2[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:20])=[O:21])[CH2:15][CH2:14]2)=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:7]=1)[NH2:8]

Komponenten

3

Edukt 1

HCID 59452727HCID 59452727, Verbindung

Produkt 1

HCID 59452788HCID 59452788, VerbindungAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21901258Dichloromethane ethyl acetate methanolLösungsmittel

Versuchsvorschrift

1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-(methylsulfonyl)piperazine (0.87 g, 2.64 mmol) was placed in a 100 mL high pressure vessel and dissolved in 60 mL of 1 to 1 to 1 EtOAc/MeOH/DCM. 5 wt % Platinum(sulfided)/C (1.03 g, 0.26 mmol) was added followed quickly by a rubber septum. The vessel was evacuated and filled with N2 six times to remove any oxygen. The vessel 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 (0.602 g, 2.01 mmol, 76%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.58 (s, 1H), 6.43 (s, 1H), 4.44 (s, 2H), 3.69 (s, 3H), 3.15-3.23 (m, 4H), 2.90 (s, 3H), 2.77-2.83 (m, 4H), 2.06 (s, 3H).

Aufarbeitung

  1. customThe vessel 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-d32f5ea37b6548bda6f89e4ac3b28985
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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