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

HRID 840137Notes

Reaction equation

HRID 840137 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-8747fed1cfcb41ef98bef676ad2983b3
Source dataset
uspto-grants-2002_04
Patent number
US06365599B1

Reaction notes

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