Water → HCID 12268076, compound

HRID 1243518Notes

Reaction equation

HRID 1243518 reaction equation
[CH3:1][C:2]1([CH2:14][CH2:15][CH3:16])[CH:7](C#N)[C:6](=[O:10])N[C:4](=[O:11])[CH:3]1C#N.[OH2:17]>S(=O)(=O)(O)O>[CH3:1][C:2]1([CH2:14][CH2:15][CH3:16])[CH2:3][C:4](=[O:11])[O:17][C:6](=[O:10])[CH2:7]1

Participants

4

Reactant 2

HCID 962WaterHCID 9585664635-91-2

Product 1

HCID 12268076HCID 12268076, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
130 °C

Procedure

Following the procedure of Vogel, A. I.; J. Chem. Soc., 1934; 1758–1765: 4-Methyl-2,6-dioxo-4-propyl-piperidine-3,5-dicarbonitrile was dissolved in 50 mL of sulfuric acid and stirred for 16 hrs. Water (50 mL) was added and the solution was refluxed for 18 hrs. Upon cooling, the crystals were collected. The crystals were suspended in 10 mL of acetic anhydride. The suspension was heated to 130° C. and stirred for 16 hrs. The solvent was removed under reduced pressure. The residue was partitioned between saturated aqueous sodium bicarbonate and diethyl ether. The ether fraction was treated with anhydrous magnesium sulfate and concentrated under reduced pressure to give the productMS (ESI+) for C9H14O3 m/z 171.2 (M+H)+.

Workup

  1. temperaturethe solution was refluxed for 18 hrs
  2. temperatureUpon cooling
  3. customthe crystals were collected
  4. stirringstirred for 16 hrs
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was partitioned between saturated aqueous sodium bicarbonate and diethyl ether
  7. additionThe ether fraction was treated with anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give the productMS (ESI+) for C9H14O3 m/z 171.2 (M+H)+

Sources & evidence

ORD record
ord-eb8dc95f2d5d4803b436be79ccba9609
Source dataset
uspto-grants-2006_10
Patent number
US07119098B2

Reaction notes

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