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

HRID 1267307

반응식

HRID 1267307 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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-oxoethoxy]phenyl]propyl]-2,4-oxazolidinedione (0.32 g, 16%) was obtained as an oily product.

후처리

  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)

출처 및 근거

ORD 기록
ord-5e799efb40eb44449e8e7643f1756a3d
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552058B1

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