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

HRID 419516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419516
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH3:21])[CH2:17][CH:18]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2]>CCOC(C)=O.CO>[CH3:2][CH2:1][O:3][C:4]1[CH:5]=[C:6]([CH:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH3:21])[CH2:17][CH2:18]2)[CH:7]=[CH:8][C:9]=1[NH2:10]

Komponenten

3

Edukt 1

HCID 594530114-[3-(Ethyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine

Produkt 1

HCID 594526052-(2-Ethyloxy)-4-(1-propyl-4-piperidinyl)anilineAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

4-[3-(ethyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine (0.536 g, 1.85 mmol) was place in a 40 mL high vial and dissolved in 10 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/carbon (0.196 g, 0.092 mmol) was added followed quickly by a screw cap septum. The vial was evacuated and filled with N2 six times to remove any oxygen. The vial was then pressurized with H2 (balloon). 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 E (0.491 g, 1.87 mmol, 99%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.61 (d, J=1.10 Hz, 1H), 6.47-6.53 (m, 2H), 4.41 (bs, 2H), 3.95 (q, J=6.96 Hz, 2H), 2.91 (d, J=10.07 Hz, 2H), 2.19-2.31 (m, 3H), 1.86-1.97 (m, 2H), 1.61-1.68 (m, 2H), 1.56 (td, J=12.18, 3.11 Hz, 2H), 1.37-1.47 (m, 2H), 1.29 (t, J=6.96 Hz, 3H), 0.83 (t, J=7.33 Hz, 3H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-5b65ba8b609846a88aa7ae7d2e7b542e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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