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

HRID 1444591Notes

Reaction equation

HRID 1444591 reaction equation
CO[CH:3]([N:6]([CH3:8])[CH3:7])OC.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>C1(C)C=CC=CC=1>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH2:18][C:19](=[O:22])[C:20](=[CH:3][N:6]([CH3:8])[CH3:7])[CH2:21]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

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 1140TolueneSolvent

Procedure

Dimethoxymethyl-dimethyl-amine (DMA) 35.5 ml (266 mmol) was added to a solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester 10.59 g (53.14 mmol) in toluene (50 ml) with stirring and with nitrogen as inert gas and refluxing was performed for 3.5 h. After removal of the solvent, the product 3-dimethylaminomethylene-4-oxo-piperidine-1-carboxylic acid tert-butyl ester was obtained, which was used in the subsequent reaction without further purification.

Workup

  1. temperaturerefluxing
  2. customAfter removal of the solvent

Sources & evidence

ORD record
ord-d77705b5a07648ab8efec8e319d0c904
Source dataset
uspto-grants-2010_02
Patent number
US07662828B2

Reaction notes

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