Acetic Acid → 11N-831

HRID 322212Notes

Reaction equation

HRID 322212 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[CH2:8]1[O:18][C:17]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=2[O:9]1.N1CCCCC1.CC(O)=O>C(O)(C)C>[CH2:8]1[O:18][C:17]2[CH:16]=[CH:15][C:12]([CH:13]=[C:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])=[CH:11][C:10]=2[O:9]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 8438PiperonalHCID 31261Acetylacetone

Product 1

HCID 24041511N-831Yield 41.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of pentane-2,4-dione (20.0 g, 200 mmol), 3,4-methylenedioxybenzaldehyde (32.2 g, 200 mmol), piperidine (1.98 mL, 20.0 mmol), and HOAc (1.20 mL, 20.0 mmol) in 200 mL of isopropanol were stirred at room temperature for 3 days (no precipitate). The solvent was remove in vacuo, and the crude product was heated to 50-70° C. under reduced pressure for 0.5 hours (no solids). The crude product was chromatographed on 900 g of silica packed with 10% EtOAc-hexane. The column was eluted with increasing amounts of EtOAc (10% to 30%, 2.5%/2 L change) to give 19.1 g (41%) of the desired product as a yellow solid: mp 79-80° C. The product was used in the next step after spectral characterization.

Workup

  1. customThe solvent was remove in vacuo
  2. temperaturethe crude product was heated to 50-70° C. under reduced pressure for 0.5 hours (no solids)
  3. customThe crude product was chromatographed on 900 g of silica
  4. washThe column was eluted with increasing amounts of EtOAc (10% to 30%, 2.5%/2 L change)

Sources & evidence

ORD record
ord-b821611d517b423ba6c49ae60d84a540
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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