HCID 59442064, compound → HCID 59442005, compound

HRID 1014178Notes

Reaction equation

HRID 1014178 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:17][N:16]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]2[CH2:13][CH2:14][CH2:15][N:16]([CH2:18][CH2:19][CH3:20])[CH2:17]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

3

Reactant 1

HCID 59442064HCID 59442064, compound

Product 1

HCID 59442005HCID 59442005, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a pressure vessel was placed 5-[3-(methyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine (Intermediate B11, 4.1 g, 15.0 mmol) in Ethyl acetate (100 mL). The solution was bubbled with nitrogen for 15 min before the addition of 10% Pd/C (0.5 g). The reaction was stirred at RT for 12 h under 60 psi of H2. After releasing H2 pressure, the mixture was filtered through celite, and the filtrate was concentrated and purified by silica gel chromatography to afford 2-(methyloxy)-4-(1-propyl-3-piperidinyl)aniline (3.5 g, 96% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.82 (t, J=7.3 Hz, 3 H), 1.27-1.45 (m, 3 H), 1.45-1.58 (m, 1 H), 1.61-1.69 (m, 1 H), 1.69-1.77 (m, 1 H), 1.77-1.89 (m, 2 H), 2.16-2.26 (m, 2 H), 2.50-2.58 (m, 1 H), 2.75-2.88 (m, 2 H), 3.72 (s, 3 H), 4.47 (s, 2 H), 6.52 (d, J=0.9 Hz, 2 H), 6.65 (s, 1 H).

Workup

  1. customIn a pressure vessel was placed
  2. customThe solution was bubbled with nitrogen for 15 min before the addition of 10% Pd/C (0.5 g)
  3. filtrationthe mixture was filtered through celite
  4. concentrationthe filtrate was concentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-2496c0afd2234d93814eac7ce0c4314e
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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