Piperidine → 5-[4-[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]butylidene]-2,4-oxazolidinedione

HRID 1857510Notes

Reaction equation

HRID 1857510 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH:25]2OCCCO2)=[CH:18][CH:17]=1.[O:31]1[CH2:35][C:34](=[O:36])[NH:33][C:32]1=[O:37].N1CCCCC1>C(O)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH2:24][CH:25]=[C:35]2[O:31][C:32](=[O:37])[NH:33][C:34]2=[O:36])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 110259022-[3-[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propyl]-1,3-dioxane

Product 1

HCID 570316105-[4-[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]butylidene]-2,4-oxazolidinedioneYield 26%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propyl]-1,3-dioxane (2.0 g), 2,4-oxazolidinedione (0.99 g), piperidine (0.21 g) and acetic acid (50 ml) was heated for 24 hours under reflux. The reaction mixture was concentrated under reduced pressure, to which was added ethyl acetate. The ethyl acetate layer was washed with an aqueous solution of sodium hydrogencarbonate, 2N HCl and water, successively, which was then dried (MgSO4), followed by concentration. The concentrate was purified by means of a silica gel column chromatography. From the fractions eluted with chloroform - ethyl acetate (5:1), 5-[4-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]butylidene]-2,4-oxazolidinedione (0.55 g, 26%) was obtained. Recrystallization from ethyl ether-methanol gave colorless needles, m.p.152-153° C.

Workup

  1. temperaturewas heated for 24 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure, to which
  4. additionwas added ethyl acetate
  5. washThe ethyl acetate layer was washed with an aqueous solution of sodium hydrogencarbonate, 2N HCl and water
  6. dry with materialsuccessively, which was then dried (MgSO4)
  7. concentrationfollowed by concentration
  8. customThe concentrate was purified by means of a silica gel column chromatography
  9. washFrom the fractions eluted with chloroform - ethyl acetate (5:1)

Sources & evidence

ORD record
ord-b9a5677c1bbe4c189ebd4dc42e9c0c8e
Source dataset
uspto-grants-2000_11
Patent number
US06147099

Reaction notes

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