Dichlone → HCID 13934742, compound

HRID 622389Notes

Reaction equation

HRID 622389 reaction equation
Cl[C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1[Cl:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[N:15]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C(O)C>[Cl:12][C:11]1[C:10](=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:14])[C:2]=1[N:18]1[CH2:17][CH2:16][N:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 8342DichloneHCID 84311-Piperazinecarboxylic acid, ethyl ester

Product 1

HCID 13934742HCID 13934742, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 11.35 g of 2,3-dichloro-1,4-naphthoquinone, 15.8 g of 1-piperazinecarboxylic acid, ethyl ester and 400 ml of absolute ethanol was heated at reflux for 3 hours and then evaporated to dryness. The residue was taken up in 300 ml of dichloromethane and filtered through silica gel. The filtrate was evaporated and the residue triturated with ether, giving 8.0 g of the desired product as red crystals, mp 120-122°C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customevaporated to dryness
  4. filtrationfiltered through silica gel
  5. customThe filtrate was evaporated
  6. customthe residue triturated with ether

Sources & evidence

ORD record
ord-736719bdf1e5437295031e442822ae79
Source dataset
uspto-grants-1988_09
Patent number
US04771061

Reaction notes

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