1-{2-[2-Fluoro-5-(methyloxy)-4-nitrophenyl]ethyl}piperidine → 5-Fluoro-2-(methyloxy)-4-[2-(1-piperidinyl)ethyl]aniline

HRID 419451Notes

Reaction equation

HRID 419451 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>CCOC(C)=O>[F:1][C:2]1[C:3]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:7]=1)[NH2:8]

Participants

3

Reactant 1

HCID 594529711-{2-[2-Fluoro-5-(methyloxy)-4-nitrophenyl]ethyl}piperidine

Product 1

HCID 594529305-Fluoro-2-(methyloxy)-4-[2-(1-piperidinyl)ethyl]anilineYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-{2-[2-fluoro-5-(methyloxy)-4-nitrophenyl]ethyl}piperidine (0.81 g, 2.87 mmol) was placed in a 100 mL high pressure vessel and dissolved in 30 mL of EtOAc. 5 wt % Platinum(sulfided)/carbon (0.559 g, 0.143 mmol) was added followed quickly by a rubber septum. The flask was evacuated and filled with N2 six times to remove 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 H2. The solution was filtered through celite and evaporated to afford the title compound of step D (0.586 g, 2.32 mmol, 81%). 1H NMR (400 MHz, CD3OD) δ ppm 6.72 (d, J=6.96 Hz, 1H), 6.46 (d, J=11.35 Hz, 1H), 3.81 (s, 3H), 3.21-3.27 (m, 2H), 3.13-3.21 (m, 4H), 2.93-2.99 (m, 2H), 1.82-1.89 (m, 4H), 1.62-1.71 (m, 2H).

Workup

  1. customThe flask was evacuated
  2. additionfilled with N2 six times
  3. customto remove oxygen
  4. customThe next morning the vessel was evacuated
  5. additionfilled with N2 six times
  6. customto remove H2
  7. filtrationThe solution was filtered through celite
  8. customevaporated

Sources & evidence

ORD record
ord-ddc04fcc29cb49c7afb545f617ea63f5
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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