Water → HCID 12268076, compound

HRID 585553Notes

Reaction equation

HRID 585553 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 product MS (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 product MS (ESI+) for C9H14O3 m/z 171.2 (M+H)+

Sources & evidence

ORD record
ord-4b1e42173ce342a1ad81e1f437b3a2f7
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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