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

HRID 911907Notes

Reaction equation

HRID 911907 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-a36c59a9d9274ad6a3bc30f24ee73277
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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