4-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine → 5-Methyl-2-(methyloxy)-4-(1-propyl-4-piperidinyl)aniline
Reaction equation
[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]Participants
Procedure
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).
Workup
- customThe flask was evacuated
- additionfilled with N2 six times
- customto remove any oxygen
- customThe next morning the vessel was evacuated
- additionfilled with N2 six times
- customto remove any H2
- filtrationThe solution was filtered through celite
- customevaporated
Sources & evidence
- ORD record
- ord-aebbb17775884ed0ab413b483a6d3623
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093239B2
Reaction notes
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