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

HRID 1052017Notes

Reaction equation

HRID 1052017 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>O1CCOCC1>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10](=[CH:1][N:8]([CH3:13])[CH3:9])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

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 312751,4-DioxaneSolvent

Procedure

A solution of N-Boc-4-piperidone (10 g, 50.19 mmol) and DMF-dimethylacetal (20.16 ml, 150.57 mmol) in 1,4-dioxane (100 ml) was heated at reflux for 20 hours. The reaction mixture was concentrated and the residue was eluted through a flash column (silica gel 60, 230-400 mesh, 7% MeOH in EtOAc) to give the title compound as an orange oil which crystallized on standing (10.51 g, 82%).

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationThe reaction mixture was concentrated
  3. washthe residue was eluted through a flash column (silica gel 60, 230-400 mesh, 7% MeOH in EtOAc)

Sources & evidence

ORD record
ord-102aeda866984240aa8085788d2e82db
Source dataset
uspto-grants-2016_07
Patent number
US09388176B2

Reaction notes

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