1-{3-[3-(Methyloxy)-4-nitrophenyl]-2-propyn-1-yl}piperidine → 2-(Methyloxy)-4-[3-(1-piperidinyl)propyl]aniline
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]#[C:13][CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CCOC(C)=O.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=[CH:7][C:8]=1[NH2:9]Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
1-{3-[3-(methyloxy)-4-nitrophenyl]-2-propyn-1-yl}piperidine (0.29 g, 1.06 mmol) was placed in a 40 mL high vial and dissolved in 10 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/carbon (0.284 g, 0.07 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 D (0.156 g, 0.63 mmol, 60%). 1H NMR (400 MHz, CDCl3) δ ppm 6.56-6.64 (m, 3H), 3.83 (s, 3H), 3.40-3.75 (m, 2H), 2.50 (dt, J=19.14, 7.55 Hz, 4H), 2.37-2.45 (m, 2H), 1.86 (dt, J=15.29, 7.74 Hz, 1H), 1.63-1.70 (m, 2H), 1.59 (ddd, J=14.97, 7.55, 1.10 Hz, 2H), 1.45 (s, 1H), 0.92 (td, J=7.33, 1.10 Hz, 2H).