Dimethylformamide dimethyl acetal → tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

HRID 1158772Notes

Reaction equation

HRID 1158772 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>CN(C)C=O>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][C:7]1=[CH:17][N:18]([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 4-oxo-1-piperidinecarboxylate (8.73 g, 44 mmol) and N,N-dimethylformamide dimethyl acetal (5.8 mL, 44 mmol) in 80 mL of dry N,N-dimethylformamide was warmed at 80° C. for 18 h. The solution was cooled and concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The mixture was filtered through a pad of Celite, and the organic layer was separated, washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound as an orange oil.

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. filtrationThe mixture was filtered through a pad of Celite
  5. customthe organic layer was separated
  6. washwashed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b6a1faa549cf404b8d11650772caccdb
Source dataset
uspto-grants-2010_10
Patent number
US07812027B2

Reaction notes

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