1-Piperazinecarboxylic acid, ethyl ester → HCID 13957253, compound

HRID 1252087Notes

Reaction equation

HRID 1252087 reaction equation
[N:1]1[C:10]2[C:9](=[O:11])[CH:8]=[CH:7][C:6](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[N:13]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>COCCOC.[Ag]=O>[CH2:22]([O:21][C:19]([N:13]1[CH2:14][CH2:15][N:16]([C:7]2[C:6](=[O:12])[C:5]3[CH:4]=[CH:3][CH:2]=[N:1][C:10]=3[C:9](=[O:11])[CH:8]=2)[CH2:17][CH2:18]1)=[O:20])[CH3:23]

Participants

5

Reactant 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 3883065,8-Dihydroquinoline-5,8-dione

Product 1

HCID 13957253HCID 13957253, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A mixture of 1.1 g of 5,8-quinolinedione in 100 ml of 1,2-dimethoxyethane was added dropwise to a solution of 2.37 g of 1-piperazinecarboxylic acid, ethyl ester in 25 ml of 1,2-dimethyoxyethane with stirring. Stirring was continued for 30 minutes, then 1 g of silver oxide was added and this mixture was stirred overnight. The mixture was filtered and the solid washed with dichloromethane. The filtrate and wash were combined, evaporated, triturated with ethyl acetate and the solid collected. This solid was chromatographed, eluting with dichloromethane, then ethyl acetate. The active fractions were combined and evaporated, giving 817 mg of the desired product, mp 192°-194° C. (dec.).

Workup

  1. stirringStirring
  2. stirringthis mixture was stirred overnight
  3. filtrationThe mixture was filtered
  4. washthe solid washed with dichloromethane
  5. washThe filtrate and wash
  6. customevaporated
  7. customtriturated with ethyl acetate
  8. customthe solid collected
  9. customThis solid was chromatographed
  10. washeluting with dichloromethane
  11. customevaporated

Sources & evidence

ORD record
ord-54d7fc83fee942fdb694d98f42828fcf
Source dataset
uspto-grants-1988_05
Patent number
US04742059

Reaction notes

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