Acetic Acid → 3-Methyl-2,6-piperidinedione

HRID 75946

Reaction equation

HRID 75946 reaction equation
OS(O)(=O)=O.[C:6]([OH:9])(=O)[CH3:7].[CH3:10][CH:11]([CH2:14]CC#N)[C:12]#[N:13].C([O-])([O-])=[O:19].[Na+].[Na+]>O>[CH3:10][CH:11]1[CH2:14][CH2:7][C:6](=[O:9])[NH:13][C:12]1=[O:19]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 206862-Methylpentanedinitrile

Product 1

HCID 346293-Methyl-2,6-piperidinedioneYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A solution of H2SO4 (80 ml), acetic acid (500 ml) and 2-methylpentanedinitrile (128.0 g, 1184 mmol) was stirred at room temperature. An aqueous solution of acetic acid (100 ml in 32 ml water) was then added dropwise. Upon completion of the addition, the reaction was heated to 130° C. for 1 hour. The reaction was then allowed to cool to room temperature and filtered to remove solids, which were washed with acetic acid (100 ml). The filtrate was then concentrated until a residue resulted. This residue was poured into water (0.75 l), and adjusted to pH 5 with Na2CO3. The resulting solid was collected by filtration and washed with cold water to give the title compound (101 g, 67%) which was used without further purification.

Workup

  1. additionUpon completion of the addition
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. customto remove solids, which
  5. washwere washed with acetic acid (100 ml)
  6. concentrationThe filtrate was then concentrated until a residue
  7. customresulted
  8. filtrationThe resulting solid was collected by filtration
  9. washwashed with cold water

Sources & evidence

ORD record
ord-faca0af8e1974591a4fb020f2178728c
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Linked notes

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