Methyl 3-(4-oxopiperidin-1-yl)benzoate → Methyl-3-(3-dimethylaminomethylene-4-oxopiperidin-1-yl)benzoate

HRID 1051985Notes

Reaction equation

HRID 1051985 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[CH:5]=1>O1CCOCC1>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][C:13](=[O:16])[C:12](=[CH:6][N:10]([CH3:15])[CH3:11])[CH2:11]2)[CH:5]=1

Participants

3

Reactant 1

HCID 60059322Methyl 3-(4-oxopiperidin-1-yl)benzoate

Product 1

HCID 86695813Methyl-3-(3-dimethylaminomethylene-4-oxopiperidin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl-3-(4-oxopiperidin-1-yl)-benzoate (2.72 g, 11.66 mmol) and DMF-dimethylacetal (6.24 mL, 46.64 mmol) in 1,4-dioxane (50 mL) was refluxed for 43 hours. The reaction mixture was concentrated and the residue was eluted through a flash column (silica gel 60, 230-400 mesh, 5% MeOH in EtOAc to 8% MeOH in EtOAc) to obtain the title compound as a red oil which slowly crystallized on standing (1.52 g, 45%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was eluted through a flash column (silica gel 60, 230-400 mesh, 5% MeOH in EtOAc to 8% MeOH in EtOAc)

Sources & evidence

ORD record
ord-aab1b8d1237b491da0ed011ce5145d53
Source dataset
uspto-grants-2016_07
Patent number
US09388176B2

Reaction notes

Loading…