4-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine → 5-Methyl-2-(methyloxy)-4-(1-propyl-4-piperidinyl)aniline

HRID 419523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419523
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[C:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH3:21])[CH2:17][CH:18]=1>CCOC(C)=O.CO>[CH3:1][C:2]1[C:3]([CH:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH3:21])[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 594529274-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine

Produkt 1

HCID 594528145-Methyl-2-(methyloxy)-4-(1-propyl-4-piperidinyl)anilineAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

4-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine (0.7 g, 2.41 mmol) was place in a 250 mL high pressure vessel and dissolved in 60 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/carbon (0.256 g, 0.12 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 (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 give the title compound of step D (0.577 g, 2.2 mmol, 91%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.57 (s, 1H), 6.37 (s, 1H), 4.37 (bs, 2H), 3.69 (s, 3H), 2.88-2.98 (m, 2H), 2.43-2.52 (m, 1H), 2.19-2.29 (m, 2H), 2.06 (s, 3H), 1.91-2.01 (m, 2H), 1.53-1.64 (m, 4H), 1.38-1.48 (m, 2H), 0.84 (t, J=7.42 Hz, 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-aebbb17775884ed0ab413b483a6d3623
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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