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

HRID 606668

Reaction equation

HRID 606668 reaction equation
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]

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-f909443f7586477887865841278719f7
Source dataset
uspto-grants-2011_03
Patent number
US07915420B2

Linked notes

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