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

HRID 2301097Notes

Reaction equation

HRID 2301097 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

N-t-Butoxycarbonyl-4-piperidone (3.0 g, 15 mmol) was dissolved in N,N-dimethylformamide dimethylacetal (15 ml) and heated under reflux for 1 hour. The solvent was removed by evaporation from the reaction solution under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 1.3 g (5.2 mmol, 34% in yield) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customThe solvent was removed by evaporation from the reaction solution under a reduced pressure
  4. customthe thus obtained material was separated
  5. custompurified by a silica gel column chromatography
  6. customto obtain

Sources & evidence

ORD record
ord-e25cac3de3da42499773018d5c8560b7
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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