Lithium iodide → 3-Methoxymethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one

HRID 1594855Notes

Reaction equation

HRID 1594855 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=2)[CH2:10][CH2:9][CH2:8][CH2:7][N:6]([CH3:11])[C:5]1=[O:12].[Li+].[I-]>N1C(C)=CC(C)=CC=1C.CCOC(C)=O>[CH3:1][O:2][CH2:3][C:4]1([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[CH2:10][CH2:9][CH2:8][CH2:7][N:6]([CH3:11])[C:5]1=[O:12]

Participants

5

Reactant 2

HCID 66321Lithium iodideHCID 217062403-Methoxymethyl-3-(3-methoxy-phenyl)-1-methyl-azepan-2-one

Product 1

HCID 217062103-Methoxymethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one

Reagents, catalysts & solvents 2

HCID 79532,4,6-TrimethylpyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methoxymethyl-3-(3-methoxy-phenyl)-1-methyl-azepan-2-one (as described in Example 6, Step A) (0.391 g, 1.48 mmol) and LiI (0.500 g, 3.73 mol) were heated in collidine (3.5 mL) at 200° C. for 10 h. The reaction mixture was cooled, diluted with EtOAc, washed with 1N HCl (2×), H2O, brine, dried (MgSO4) and concentrated to give the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with 1N HCl (2×), H2O, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-892a43c948ea454692ac64f3f3fef2fe
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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