Water → 4-piperidino-3-[3-[3-(2-methylthioethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one

HRID 639739Notes

Reaction equation

HRID 639739 reaction equation
[C:1]([C:4]1[C:5](=[O:12])[O:6][C:7]([CH3:11])=[CH:8][C:9]=1O)(=[O:3])[CH3:2].[CH3:13][S:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.O>C(Cl)(Cl)Cl>[N:26]1([C:9]2[CH:8]=[C:7]([CH3:11])[O:6][C:5](=[O:12])[C:4]=2[C:1](=[O:3])[CH:2]=[CH:21][C:20]2[CH:23]=[CH:24][CH:25]=[C:18]([O:17][CH2:16][CH2:15][S:14][CH3:13])[CH:19]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 231317123-(2-Methylthioethoxy)benzaldehydeHCID 546784943-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

Product 1

HCID 686767284-piperidino-3-[3-[3-(2-methylthioethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-oneYield 6.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 8 ml of chloroform were dissolved 85.7 mg of 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one, 100 mg of 3-(2-methylthioethoxy)benzaldehyde and 30.3 mg of piperidine, and the solution was heated under refluxing for 13 hours while water was removed with a Soxhlet's extractor filled with a molecular sieve. After cooling to room temperature, the reaction mixture washed successively with 10% hydrochloric acid and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated. Precipitated crystals were filtered, and this was subjected to silica gel column chromatography to obtain 10.1 mg of 4-piperidino-3-[3-[3-(2-methylthioethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one [Compound No. (14b)] as a pale yellow crystal.

Workup

  1. temperaturethe solution was heated
  2. customwas removed with a Soxhlet's extractor
  3. additionfilled with a molecular sieve
  4. washthe reaction mixture washed successively with 10% hydrochloric acid
  5. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customPrecipitated crystals
  8. filtrationwere filtered

Sources & evidence

ORD record
ord-934c1954b5144109b3eb6659a3e30f33
Source dataset
uspto-grants-2010_04
Patent number
US07691883B2

Reaction notes

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