3-Ethyl-3-(3-methoxyphenyl)azepan-2-one → 3-Ethyl-3-(3-methoxy-phenyl)-azepane

HRID 429068Notes

Reaction equation

HRID 429068 reaction equation
[CH2:1]([C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]1=O)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 28154553-Ethyl-3-(3-methoxyphenyl)azepan-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 109114603-Ethyl-3-(3-methoxy-phenyl)-azepane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Ethyl-3-(3-methoxy-phenyl)-azepan-2-one (as described in Step H above) (1.05 g, 4.24 mmol) in anhydrous THF (4.2 mL) was added to a solution of LiAlH4 (0.193 g, 5.09 mmol) in anhydrous THF (4.2 mL) and refluxed for 24 h. The solution was cooled, quenched with H2O (0.18 mL), 15% NaOH (0.18 mL), H2O (0.54 mL), filtered and concentrated. The residue was purified using reverse phase chromatography (95/5-5/95 H2O/CH3CN with 0.1% TFA, flow =65 mL/min) and converted to its free base using saturated NaHCO3 solution, extracted with CH2Cl2 (3×) and dried (MgSO4) to give the title compound.

Workup

  1. temperaturerefluxed for 24 h
  2. temperatureThe solution was cooled
  3. customquenched with H2O (0.18 mL), 15% NaOH (0.18 mL), H2O (0.54 mL)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. extractionextracted with CH2Cl2 (3×)
  8. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-74947146890549cd9b1c2fa21c68b8be
Source dataset
uspto-grants-2001_11
Patent number
US06316436B1

Reaction notes

Loading…