1-acetyl-N-methoxy-N-methylpiperidine-4-carboxamide → 1,4-Diacetylpiperidine

HRID 335229Notes

Reaction equation

HRID 335229 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](N(OC)C)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:16][Mg]Br>C1COCC1>[N:4]1([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6][CH:7]([C:10](=[O:11])[CH3:16])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 187135481-acetyl-N-methoxy-N-methylpiperidine-4-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 27772501,4-DiacetylpiperidineYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-Acetyl-N-methoxy-N-methylpiperidine-4-carboxamide (59.10 g, 276 mmol) was dissolved in THF (800 mL) and cooled to 0° C. Methylmagnesium bromide (110.3 mL, 331 mmol) (3.0M in diethyl ether) was added slowly and the resulting white slurry was agitated for 1 hour. The reaction was quenched with 300 mL of 2M HCl and the solvent was evaporated. The resulting aqueous slurry was filtered and the solids were washed with water and small amount of ether to provide the title compound (38.4 g, 82.2% yield).

Workup

  1. customThe reaction was quenched with 300 mL of 2M HCl
  2. customthe solvent was evaporated
  3. filtrationThe resulting aqueous slurry was filtered
  4. washthe solids were washed with water and small amount of ether

Sources & evidence

ORD record
ord-89e4189071c443b4bdd0d4fe1bcdbe85
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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