4-(3-Methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine → 2-Methoxy-4-(1-propylpiperidin-4-yl)aniline

HRID 419475Notes

Reaction equation

HRID 419475 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][CH3:20])[CH2:16][CH:17]=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]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

3

Reactant 1

HCID 598602684-(3-Methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine

Product 1

HCID 598602732-Methoxy-4-(1-propylpiperidin-4-yl)anilineYield 80.2%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

4-[3-(methyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine (3.33 g, 12.05 mmol) was placed in a 250 mL high pressure vessel and dissolved in 60 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/C (4.7 g, 1.2 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 (50 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 (2.4 g, 9.66 mmol, 80%). 1H NMR (400 MHz, CDCl3) δ ppm 6.68 (s, 1H), 6.63 (s, 2H), 3.81 (s, 3H), 3.52 (bs, 2H), 3.07 (d, J=11.90 Hz, 2H), 2.40 (s, 1H), 2.32-2.38 (m, 2H), 1.98-2.07 (m, 2H), 1.80 (ddd, J=12.32, 6.00, 3.30 Hz, 4H), 1.51-1.61 (m, 2H), 0.91 (t, J=7.42 Hz, 3H).

Workup

  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

Sources & evidence

ORD record
ord-f29c5c4ced3c4d82b1c1fb24a1c7cd40
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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