Ethanol → HCID 70009761, compound

HRID 1267309Notes

Reaction equation

HRID 1267309 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 (2.86 g), 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-d5e7f08f9cba43d984566523cfd27acc
Source dataset
uspto-grants-2003_04
Patent number
US06552058B1

Reaction notes

Loading…