Hydrochloric Acid → N-methoxy-N-methyl-2-oxopiperidine-4-carboxamide

HRID 535314Notes

Reaction equation

HRID 535314 reaction equation
[O:1]=[C:2]1[CH2:7][CH:6]([C:8]([OH:10])=O)[CH2:5][CH2:4][NH:3]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:23][NH:24][O:25][CH3:26].Cl.O1CCOCC1>C(Cl)Cl>[CH3:26][O:25][N:24]([CH3:23])[C:8]([CH:6]1[CH2:5][CH2:4][NH:3][C:2](=[O:1])[CH2:7]1)=[O:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14232N,O-DimethylhydroxylamineHCID 312751,4-DioxaneHCID 682631,1'-CarbonyldiimidazoleHCID 552860802-Oxopiperidine-4-carboxylic acid

Product 1

HCID 86718437N-methoxy-N-methyl-2-oxopiperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-oxopiperidine-4-carboxylic acid (CAS #24537-50-6) (1.4 g, 9.78 mmol) in DCM (20 ml) was added portion wise CDI (1.665 g, 10.27 mmol). The suspension was stirred at room temperature for 5 hrs and N,O-dimethylhydroxylamine (1.002 g, 10.27 mmol) was added to the suspension and the reaction mixture was stirred overnight at room temperature. HCl (4M) in 1,4-dioxane (2.445 ml, 9.78 mmol) was added to the cloudy brown-orange solution and the reaction was stirred for 30 min (pH 7). The white precipitate was filtered off and the filtrate was washed with aqueous NaHCO3 solution. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to obtain the title compound as brown liquid.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. stirringthe reaction was stirred for 30 min (pH 7)
  3. filtrationThe white precipitate was filtered off
  4. washthe filtrate was washed with aqueous NaHCO3 solution
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e91d84a9492f45df90da9a2496b8bc82
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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