Methanol → 2-Methoxy-4-(1-propylpiperidin-4-yl)aniline

HRID 1014191Notes

Reaction equation

HRID 1014191 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.CO>[Pd].C(OCC)(=O)C>[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

5

Reactant 2

HCID 887MethanolHCID 598602684-(3-Methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine

Product 1

HCID 598602732-Methoxy-4-(1-propylpiperidin-4-yl)anilineYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on carbon (10% by weight, 2.5 g) was added to a nitrogen-flushed Fischer-Porter vessel. At least a portion of the 4-(3-methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine from Step B was combined with additional 4-(3-methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine prepared by substantially the same method. Then, a solution of the 4-(3-methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine (9.20 g, 33.3 mmol) in Ethyl acetate (150 mL) followed by methanol (50 mL) were added to the vessel. The reaction was purged and then kept under a hydrogen pressure of 60 psi for 2 d. The pressure was released and the reaction was purged with nitrogen. The reaction was filtered through celite and concentrated to afford 2-methoxy-4-(1-propylpiperidin-4-yl)aniline as a white solid (7.0 g, 85% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.86 (t, J=7.5 Hz, 3 H), 1.44 (dt, J=7.4, 7.4 Hz, 2 H), 1.52-1.63 (m, 2 H), 1.63-1.70 (m, 2 H), 1.90 (td, J=11.6, 2.4 Hz, 2 H), 2.20-2.25 (m, 2 H), 2.30 (tt, J=11.9, 4.0 Hz, 1 H), 2.89-2.94 (m, 2 H), 3.74 (s, 3 H), 4.45 (s, 2 H), 6.53 (s, 2 H), 6.65 (s, 1 H). ESIMS (M+H)+=249.

Workup

  1. customflushed Fischer-Porter vessel
  2. customprepared by substantially the same method
  3. additionwere added to the vessel
  4. customThe reaction was purged
  5. customfor 2 d
  6. customthe reaction was purged with nitrogen
  7. filtrationThe reaction was filtered through celite
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d070b40732de4b56b3950a251e0a20f3
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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