Dimethylformamide dimethyl acetal → tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

HRID 1052007Notes

Reaction equation

HRID 1052007 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].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>O1CCOCC1>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10](=[CH:17][N:18]([CH3:20])[CH3:19])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 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 (10.0 g, 50.19 mmol) and N,N-dimethylformamide dimethylacetal (20.16 mL, 150.57 mmol) in 1,4-dioxane (100 mL) was heated at reflux for 15 hours. The solvent was removed in vacuo and the residue was eluted through a flash column (silica gel 60, 230-400 mesh, 8% MeOH in EtOAc) to obtain the title compound as an orange oil which crystallized on standing (7.64 g, 60%).

Workup

  1. temperatureat reflux for 15 hours
  2. customThe solvent was removed in vacuo
  3. washthe residue was eluted through a flash column (silica gel 60, 230-400 mesh, 8% MeOH in EtOAc)

Sources & evidence

ORD record
ord-be94d75abd9c443888c4129a67aeea11
Source dataset
uspto-grants-2016_07
Patent number
US09388176B2

Reaction notes

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