Piperidine → HCID 76211114, compound

HRID 38301

Reaction equation

HRID 38301 reaction equation
[C:1]([C:4]1[C:5](=[O:15])[O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[OH:10])(=[O:3])[CH3:2].[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=O.N1CCCCC1>C(Cl)(Cl)Cl>[OH:10][C:9]1[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[O:6][C:5](=[O:15])[C:4]=1[C:1](=[O:3])[CH:2]=[CH:20][C:19]1[CH:22]=[CH:23][C:24]([O:25][C:26]([F:27])([F:28])[F:29])=[C:17]([Cl:16])[CH:18]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 27788913-Chloro-4-(trifluoromethoxy)benzaldehydeHCID 546774033-Acetyl-4-hydroxy-2H-chromen-2-one

Product 1

HCID 76211114HCID 76211114, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2.25 g of 3-acetyl-4-hydroxy-2H-1-benzopyran-2-one, 2.25 g of 3-chloro-4-(trifluoromethoxy)benzaldehyde, 20 ml of chloroform and 0.7 ml of piperidine was heated under refluxing for 2 hours and 30 minutes. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure, and the residue was subjected to column chromatography. Resulting crystals were washed with 40 ml of t-butyl methyl ether to obtain 1.49 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one [Compound No. (1c-6)] was obtained as a yellow crystal.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 2 hours and 30 minutes
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customResulting crystals
  5. washwere washed with 40 ml of t-butyl methyl ether

Sources & evidence

ORD record
ord-f556d4fe01f1480cb1a856a18b6c926a
Source dataset
uspto-grants-2013_09
Patent number
US08524729B2

Linked notes

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