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

HRID 419451ノート

反応式

HRID 419451 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ddc04fcc29cb49c7afb545f617ea63f5
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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