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

HRID 2383422Notes

Reaction equation

[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH3:15][N:16]([CH:18](OC)OC)[CH3:17]>CN(C=O)C>[CH3:15][N:16]([CH:18]=[C:7]1[C:2](=[O:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6]1)[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (10 g, 50.25 mmol) in DMF (500 mL) at room temperature was added DMF-DMA (14.9 g, 125.62 mmol). The reaction mixture was heated at 100° C. for 48 hours. After completion of reaction the solvent was removed under reduced pressure and the resulting residue dissolved in EtOAc (300 mL) and extracted with water (2×200 mL). This organic layer was dried using sodium sulfate and concentrated under reduced pressure to give crude desired product, tert-butyl 3-((dimethylamino)methylene)-4-oxopiperidine-1-carboxylate (10.2 g, 79%), which was used in the next step without any further purification. LCMS [M+H]:255.

Workup

customAfter completion of reaction the solvent
customwas removed under reduced pressure
dissolutionthe resulting residue dissolved in EtOAc (300 mL)
extractionextracted with water (2×200 mL)
customThis organic layer was dried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-49dd2ae45ae9436d9f93fe5fe84a30f5
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263610B2

Reaction notes

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