Acetic Acid → HCID 383402, compound

HRID 582205Notes

Reaction equation

HRID 582205 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH:13](=[C:8]1[CH2:7][C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]1=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 8082PiperidineHCID 3340366-Methoxy-1-Indanone

Product 1

HCID 383402HCID 383402, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Methoxy-1-indanone (10 g, 61.2 mmol), benzaldehyde (7.85 g, 74.0 mmol), piperidine (1.05 g, 12.3 mmol), and acetic acid (4.4 g, 74.0 mmol) were refluxed in toluene (150 ml) for 3 hours. After the reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The extract was washed serially with saturated saline and water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The resulting crystals were washed with diethyl ether to provide the title compound (yield 2.3 g, 80%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed serially with saturated saline and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. washThe resulting crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-fb4a4ebe2d8b48d2ba59809d6c3dadbe
Source dataset
uspto-grants-1999_07
Patent number
US05922771

Reaction notes

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