Piperidine → HCID 57054742, compound

HRID 977261Notes

Reaction equation

HRID 977261 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][C:9]2[CH:18]=[CH:17][C:12]([CH:13]=[CH:14][CH:15]=O)=[CH:11][CH:10]=2)=[N:4][C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[O:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31].N1CCCCC1>C(O)C>[CH3:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][C:9]2[CH:18]=[CH:17][C:12]([CH:13]=[CH:14][CH:15]=[C:29]3[O:25][C:26](=[O:31])[NH:27][C:28]3=[O:30])=[CH:11][CH:10]=2)=[N:4][C:3]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 53720755HCID 53720755, compound

Product 1

HCID 57054742HCID 57054742, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2-(5-methyl-4-phenyl-2-thiazolyl)ethyl]cinnamaldehyde (2.5 g), 2,4-oxazolidinedione (1.14 g), piperidine (0.211 g) and ethanol (50 ml) was refluxed under heating conditions for 4 hours. After the reaction mixture was concentrated, chloroform was added to the residue; the mixture was washed with 2 N HCl and water. The chloroform layer was washed with water, dried (MgSO4) and then concentrated to yield 5-[4-[2-(5-methyl-4-phenyl-2-thiazolyl)ethyl]cinnamylidene]-2,4-oxazolidinedione[mixture of the (E)- and (Z)- configurations](0.81 g, 26%), which was then recrystallized from ethyl acetate to yield light yellow prisms having a melting point of 161°-162° C.

Workup

  1. temperaturewas refluxed under heating conditions for 4 hours
  2. concentrationAfter the reaction mixture was concentrated
  3. additionchloroform was added to the residue
  4. washthe mixture was washed with 2 N HCl and water
  5. washThe chloroform layer was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1e4b4e8ed0cc47d69cd333423f2b7e99
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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