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

HRID 1806155Notes

Reaction equation

HRID 1806155 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-49559709607047b2b0f85d8efdac682f
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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