Piperidine → HCID 86754365, compound

HRID 1584294Notes

Reaction equation

HRID 1584294 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:18][CH:19]=1)[CH:6]=[CH:7][CH:8]=O.[O:26]1[CH2:30][C:29](=[O:31])[NH:28][C:27]1=[O:32].N1CCCCC1>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:18][CH:19]=1)[CH:6]=[CH:7][CH:8]=[C:30]1[O:26][C:27](=[O:32])[NH:28][C:29]1=[O:31]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 53961498HCID 53961498, compound

Product 1

HCID 86754365HCID 86754365, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-methoxy-4-(2-phenyl-4-oxazolylmethoxy)cinnamaldehyde (5.5 g), 2,4-oxazolidinedione (6.7 g), piperidine (1.4 g) and acetic acid (120 ml) was stirred for three days under reflux. The reaction mixture was cooled, and resulting crystalline precipitate was collected by filtration, which was washed with water, ethanol and isopropyl ether, successively to give 5-[3-methoxy-4-(2-phenyl-4-oxazolylmethoxy)cinnamylidene]-2,4-oxazolidinedione (2.9 g, 43%), which was recrystallized from chloroform-methanol to afford yellow needles, m.p.227-228° C.

Workup

  1. temperatureunder reflux
  2. temperatureThe reaction mixture was cooled
  3. customresulting crystalline precipitate
  4. filtrationwas collected by filtration, which
  5. washwas washed with water, ethanol and isopropyl ether

Sources & evidence

ORD record
ord-49d90e6286d5412295b920fe3d1a7bf9
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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