4-[3-(Ethyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine → 2-(2-Ethyloxy)-4-(1-propyl-4-piperidinyl)aniline

HRID 419516ノート

反応式

HRID 419516 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH3:21])[CH2:17][CH:18]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2]>CCOC(C)=O.CO>[CH3:2][CH2:1][O:3][C:4]1[CH:5]=[C:6]([CH:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH3:21])[CH2:17][CH2:18]2)[CH:7]=[CH:8][C:9]=1[NH2:10]

参加物

3

反応物 1

HCID 594530114-[3-(Ethyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine

生成物 1

HCID 594526052-(2-Ethyloxy)-4-(1-propyl-4-piperidinyl)aniline収率 101.1%

試薬・触媒・溶媒 1

HCID 21584119Ethylacetate methanol溶媒

実験手順

4-[3-(ethyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine (0.536 g, 1.85 mmol) was place in a 40 mL high vial and dissolved in 10 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/carbon (0.196 g, 0.092 mmol) was added followed quickly by a screw cap septum. The vial was evacuated and filled with N2 six times to remove any oxygen. The vial was then pressurized with H2 (balloon). The solution stirred overnight. The next morning the vessel was evacuated and filled with N2 six times to remove any H2. The solution was filtered through celite and evaporated to afford the title compound of step E (0.491 g, 1.87 mmol, 99%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.61 (d, J=1.10 Hz, 1H), 6.47-6.53 (m, 2H), 4.41 (bs, 2H), 3.95 (q, J=6.96 Hz, 2H), 2.91 (d, J=10.07 Hz, 2H), 2.19-2.31 (m, 3H), 1.86-1.97 (m, 2H), 1.61-1.68 (m, 2H), 1.56 (td, J=12.18, 3.11 Hz, 2H), 1.37-1.47 (m, 2H), 1.29 (t, J=6.96 Hz, 3H), 0.83 (t, J=7.33 Hz, 3H).

後処理

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

出典と根拠

ORDレコード
ord-5b65ba8b609846a88aa7ae7d2e7b542e
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

読み込み中…