Piperidine → 2-(4-pyridylmethylene) indan-1,3-dione

HRID 1862039Notes

Reaction equation

HRID 1862039 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[CH2:2]1.N1CCCCC1.[N:18]1[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=1>>[N:18]1[CH:23]=[CH:22][C:21]([CH:24]=[C:2]2[C:1](=[O:11])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]2=[O:10])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 8082PiperidineHCID 118151,3-IndandioneHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 27327312-(4-pyridylmethylene) indan-1,3-dione

Procedure

A mixture of indane-1,3-dione (5.85 g), piperidine (0.46 ml) and pyridine-4-carboxaldehyde (4.31 g) was stirred in IMS (40 ml) at ambient temperature for 50 minutes. The mixture was cooled in an ice-bath but no crystallization occurred. The solution was allowed to warm to ambient temperature and then the solvent was removed under reduced pressure to give a residue which was partially purified by flash column chromatography on silica using 10% industrial methylated spirit in dichloromethane followed by 20% industrial methylated spirit in dichloromethane as the mobile phases. The leading fractions were collected, combined and evaporated to give a solid which was triturated with ice-cold diethyl ether and filtered to give 2-(4-pyridylmethylene) indan-1,3-dione, m.p. 152-157° C.

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. customno crystallization
  3. customthe solvent was removed under reduced pressure
  4. customto give a residue which
  5. customwas partially purified by flash column chromatography on silica using 10% industrial methylated spirit in dichloromethane
  6. customThe leading fractions were collected
  7. customevaporated
  8. customto give a solid which
  9. customwas triturated with ice-cold diethyl ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-abbee2548d7c4919923cc24560c5c654
Source dataset
uspto-grants-2003_03
Patent number
US06534655B1

Reaction notes

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