p-Toluenesulfonic acid → HCID 70155581, compound

HRID 1700359Notes

Reaction equation

HRID 1700359 reaction equation
[O:1]=[C:2]([CH2:14][CH3:15])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O.N1CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.O>[C:2]([C:3](=[CH:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([Cl:16])[CH:18]=1)[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])(=[O:1])[CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 12425357HCID 12425357, compound

Product 1

HCID 70155581HCID 70155581, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

1.59 g (7.71 mmol) of benzyl 3-oxovalerate, 1.08 g (7.71 mmol) of 3-chlorobenzaldehyde and 65.7 mg (0.771 mmol) of piperidine were heated under reflux in the presence of a catalytic amount of p-toluenesulfonic acid in 50 ml of benzene for 6 hours while water was removed. Benzene was evaporated under reduced pressure. Ethyl acetate was added to the reaction mixture. After washing with 1 N hydrochloric acid and then with a saturated aqueous sodium hydrogencarbonate solution, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1) to obtain the title compound.

Workup

  1. customwas removed
  2. customBenzene was evaporated under reduced pressure
  3. additionEthyl acetate was added to the reaction mixture
  4. washAfter washing with 1 N hydrochloric acid
  5. dry with materialwith a saturated aqueous sodium hydrogencarbonate solution, the organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-21fa53fb812a4a5b9347d17d25d41f84
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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