Piperidine → HCID 69831104, compound

HRID 1584306Notes

Reaction equation

HRID 1584306 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]2OCCO2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16].[O:33]1[CH2:37][C:36](=[O:38])[NH:35][C:34]1=[O:39].N1CCCCC1>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[C:37]2[O:33][C:34](=[O:39])[NH:35][C:36]2=[O:38])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 21224498HCID 21224498, compound

Product 1

HCID 69831104HCID 69831104, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-[5-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]pentyl]-1,3-dioxolan (3.6 g), 2,4-oxazolidinedione (1.7 g), piperidine (0.72 g) and acetic acid (50 ml) was stirred for 16 hours under reflux. The reaction mixture was concentrated under reduced pressure, which was dissolved in ethyl acetate. The solution was successively washed with a saturated aqueous solution of sodium hydrogencarbonate, water, 1N HCl and water, followed by drying (MgSO4). The ethyl acetate layer was concentrated under reduced pressure, which was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-methanol (50:1), was obtained 5-[6-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]hexylidene]-2,4-oxazolidinedione as an oily product. The oily product was dissolved in tetrahydrofuran (THF) (80 ml), to which was added palladium-carbon (5%, 1.0 g). The mixture was subjected to catalytic hydrogenation under 1 atmospheric pressure at room temperature. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-methanol (50:1), was obtained 5-[6-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]hexyl]-2,4-oxazolidinedione, which was recrystallized from ethyl acetate-isopropyl ether to give colorless prisms, m.p.113-117° C.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure, which
  3. dissolutionwas dissolved in ethyl acetate
  4. washThe solution was successively washed with a saturated aqueous solution of sodium hydrogencarbonate, water, 1N HCl and water
  5. dry with materialby drying (MgSO4)
  6. concentrationThe ethyl acetate layer was concentrated under reduced pressure, which
  7. washFrom the fraction eluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-e74be4b6f6ac4ffd9251f92ced1a0eb3
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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