tert-Butyl 4-oxopiperidine-1-carboxylate → tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

HRID 1193352Notes

Reaction equation

HRID 1193352 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>COC(OC)N(C)C>[CH3:4][N:5]([CH:8]=[C:7]1[C:2](=[O:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6]1)[CH3:6]

Participants

3

Reactant 1

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A mixture of tert-butyl 4-oxopiperidine-1-carboxylate (20.0 g, 100.38 mmol, 1.0 eq.) and N,N-dimethylformamide dimethylacetal (80 ml) was refluxed for 6 hours. After monitoring by thin-layer chromatography, the reaction mixture was concentrated under reduced pressure and the residue was taken up in DCM (300 ml), washed with water (200 ml) and sat. NaCl solution (200 ml), dried over sodium sulfate, concentrated and purified by column chromatography (silica gel, 2.5% MeOH in DCM). Yield: 40% (10.2 g, 40.16 mmol)

Workup

  1. temperaturewas refluxed for 6 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. washwashed with water (200 ml) and sat. NaCl solution (200 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica gel, 2.5% MeOH in DCM)

Sources & evidence

ORD record
ord-20dd1944c1c34b2ea53bf7e147127bf2
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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