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

HRID 2250204Notes

Reaction equation

HRID 2250204 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>COC(OC)N(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[O:14])[C:12](=[CH:6][N:8]([CH3:13])[CH3:9])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (10 g, 50 mmol) was dissolved in dimethyl formamide dimethylacetal (50 mL) and heated to reflux for 1.25 h. The solution was cooled, concentrated, and purified by flash chromatography to give 2.55 g (19%). Mass spec.: 255.16 (MH)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.25 h
  3. temperatureThe solution was cooled
  4. concentrationconcentrated
  5. custompurified by flash chromatography
  6. customto give 2.55 g (19%)

Sources & evidence

ORD record
ord-4a052ec4819f4b798634f3557870ca98
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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