Ethanol → (3-{[3-(2-Isopropoxy-phenoxy)-propylamino]-methyl}-phenyl)-piperidin-1-yl-methanone

HRID 1178773ノート

反応式

HRID 1178773 の反応式
C(O[C:5]1[CH:15]=[CH:14][CH:13]=[CH:12]C=1OCCCN)(C)C.[CH:16]([O:19][C:20]1[CH:40]=[CH:39][CH:38]=[CH:37][C:21]=1[O:22][CH2:23][CH2:24][CH2:25][N:26]1[C:34](=O)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)C1=O)([CH3:18])[CH3:17].[NH2:41]N.C[CH2:44][OH:45]>>[CH:16]([O:19][C:20]1[CH:40]=[CH:39][CH:38]=[CH:37][C:21]=1[O:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:34][C:33]1[CH:32]=[C:31]([C:44]([N:41]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:5]2)=[O:45])[CH:30]=[CH:29][CH:28]=1)([CH3:17])[CH3:18]

参加物

5

反応物 4

HCID 702EthanolHCID 9321HydrazineHCID 670459232-[3-(2-Isopropoxy-phenoxy)-propyl]-isoindole-1,3-dioneHCID 670460603-(2-Isopropoxy-phenoxy)-propylamine

生成物 1

HCID 11258388(3-{[3-(2-Isopropoxy-phenoxy)-propylamino]-methyl}-phenyl)-piperidin-1-yl-methanone収率 45%

反応条件

温度
50 °C

実験手順

3-(2-Isopropoxy-phenoxy)-propylamine. To a solution of 2-[3-(2-isopropoxy-phenoxy)-propyl]-isoindole-1,3-dione in EtOH (6 mL) was added hydrazine (0.448 g, 14.0 mmol), and the reaction mixture was heated to 50° C. for 30 min. The solvent was removed under reduced pressure, and the crude residue was partitioned between CH2Cl2 (50 mL) and H2O (50 mL). The aqueous layer was extracted with CH2Cl2 (3×50 mL), and the combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (20-50% EtOAc/hexanes) to provide the desired product (0.267 g, 45%). MS (ESI): mass calculated for C12H19NO2, 209.29. m/z found, 210.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 6.91-6.83 (m, 4H), 4.46 (hept, J=6.1 Hz, 1H), 4.07 (t, J=5.9 Hz, 2H), 2.97 (t, J=6.5 Hz, 2H), 1.99 (quint, J=6.2 Hz, 2H), 1.32 (d, J=6.1 Hz, 6H).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe crude residue was partitioned between CH2Cl2 (50 mL) and H2O (50 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×50 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by column chromatography (20-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-fd1904a055c94596a48360254346c4f2
出典データセット
uspto-grants-2007_10
特許番号
US07276610B2

反応ノート

読み込み中…