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

HRID 2355892Notes

Reaction equation

HRID 2355892 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-dfede5ba07794b1b8d16da6685225cc9
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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