Piperidine → 5-[3-[4-(2-(5-Methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy)phenyl]propylidene]-2,4-oxazolidinedione

HRID 1857516Notes

Reaction equation

HRID 1857516 reaction equation
O1CCO[CH:2]1[CH2:6][CH2:7][C:8]1[CH:29]=[CH:28][C:11]([O:12][CH2:13][C:14]([C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[O:15])=[CH:10][CH:9]=1.[O:30]1[CH2:34][C:33](=[O:35])[NH:32][C:31]1=[O:36].N1CCCCC1>C(O)(=O)C>[CH3:21][C:20]1[O:19][C:18]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[N:17][C:16]=1[C:14](=[O:15])[CH2:13][O:12][C:11]1[CH:28]=[CH:29][C:8]([CH2:7][CH2:6][CH:2]=[C:34]2[O:30][C:31](=[O:36])[NH:32][C:33]2=[O:35])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 185461704-[4-[2-(1,3-Dioxolan-2-yl)ethyl]phenoxyacetyl]-5-methyl-2-phenyloxazole

Product 1

HCID 572491385-[3-[4-(2-(5-Methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy)phenyl]propylidene]-2,4-oxazolidinedione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-[4-[2-(1,3-dioxolan-2-yl)ethyl]phenoxyacetyl]-5-methyl-2-phenyloxazole (1.8 g), 2,4-oxazolidinedione (0.925 g), piperidine (0.12 g) and acetic acid (30 ml) was heated for 15 hours under reflux. The reaction mixture was concentrated under reduced pressure. To the concentrate was added a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform. The chloroform layer was washed with water, dried (MgSO4), followed by distilling off the solvent. The oily residue was subjected to a silica gel column chromatography. From the fractions eluted with methanol-chloroform (1:30, v/v) was obtained 5-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]phenyl]propylidene]-2,4-oxazolidinedione. This compound was dissolved in tetrahydrofuran (THF) (30 ml), to which was added palladium-carbon (5%, 0.3 g). The mixture was subjected to catalytic hydrogenation. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The oily residue was subjected to a silica gel column chromatography. From the fractions eluted with ethyl acetate-hexane (1:1, v/v), 5-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxyaphenyl]propyl]-2,4-oxazolidinedione (0.32 g, 16%) was obtained as an oily product.

Workup

  1. temperaturewas heated for 15 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the concentrate was added a saturated aqueous solution of sodium hydrogencarbonate
  5. extractionfollowed by extraction with chloroform
  6. washThe chloroform layer was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationby distilling off the solvent
  9. washFrom the fractions eluted with methanol-chloroform (1:30, v/v)

Sources & evidence

ORD record
ord-db858c228bdc4c6ba9087a07607c8217
Source dataset
uspto-grants-2000_11
Patent number
US06147099

Reaction notes

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