Ethanol → HCID 70009761, compound

HRID 1377646Notes

Reaction equation

HRID 1377646 reaction equation
[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([CH:16]=[CH:17][CH:18]=O)=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[O:22]1[CH2:26][C:25](=[O:27])[NH:24][C:23]1=[O:28].N1CCCCC1.C(O)C>O1CCCC1>[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([CH2:16][CH2:17][CH2:18][CH:26]2[O:22][C:23](=[O:28])[NH:24][C:25]2=[O:27])=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 53665008HCID 53665008, compound

Product 1

HCID 70009761HCID 70009761, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]cinnamaldehyde (4.00 g), 2,4-oxazolidinedione (2.86g), piperidine (0.60 g) and ethanol (50 ml) was heated for 2 hours under reflux. The reaction mixture was concentrated and the residue was subjected to silica gel column chromatography. Fractions eluted with ethyl acetate-chloroform (1:4) gave crystals. The crystals were dissolved in tetrahydrofuran (100 ml). To the solution was added palldium-carbon (5%, 1.40 g). The mixture was subjected to catalytic hydrogenation at room temperature under atmospheric pressure. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography. From the fractions eluted with chloroform-methanol (100:2), 5-[3-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]phenyl]propyl]-2,4-oxazolidinedione (1.10 g, 21%) was obtained. Recrystallization from dichloromethane-isopropylether gave colorless prisms. Melting point: 126°-127° C.

Workup

  1. temperaturewas heated for 2 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated
  4. washFractions eluted with ethyl acetate-chloroform (1:4)
  5. customgave crystals
  6. customwas subjected to catalytic hydrogenation at room temperature under atmospheric pressure
  7. filtrationThe catalyst was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. washFrom the fractions eluted with chloroform-methanol (100:2)

Sources & evidence

ORD record
ord-850a25dfac574997bd5c87b3f9ef2a2e
Source dataset
uspto-grants-1997_09
Patent number
US05665748

Reaction notes

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