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

HRID 480560Notes

Reaction equation

HRID 480560 reaction equation
[CH3:1][N:2]([CH:4](OC)OC)[CH3:3].[C:9]([N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>CN(C=O)C>[C:12]([O:11][C:9]([N:16]1[CH2:21][CH2:20][C:19](=[O:22])[C:18](=[CH:1][N:2]([CH3:4])[CH3:3])[CH2:17]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

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)-pyridinecarboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

DMF dimethyl acetal (5.82 ml, 0.044 mol) was added to a stirred solution of 1-boc-4-piperidone [Ashwood et al., J. Chem. Soc., Perkin 1, 641 (1995)] (8.73 g, 0.044 mol) in DMF (80 ml) and the reaction mixture was heated to 80° C. under N2 for 18 h. After cooling, the DMF was removed under reduced pressure and the residue was partitioned between EtOAc and H2O, the organic layer washed with H2O and saturated brine, then dried over MgSO4 and evaporated to afford the subtitle compound as a solid (8.44 g, 76%). Rf 0.33 (CH2Cl2/MeOH/0.88NH3 90/10/1, v/v). MS m/z 255 (MH+).

Workup

  1. temperatureAfter cooling
  2. customthe DMF was removed under reduced pressure
  3. customthe residue was partitioned between EtOAc and H2O
  4. washthe organic layer washed with H2O and saturated brine
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-16c97a64f8c84c3c8a104bd8beef5c83
Source dataset
uspto-grants-2003_11
Patent number
US06653302B2

Reaction notes

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