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

HRID 419451노트

반응식

HRID 419451 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ddc04fcc29cb49c7afb545f617ea63f5
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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