Acetamide, N-(1,4-dihydro-3-chloro-1,4-dioxo-2-naphthyl)- → HCID 2926585, compound

HRID 1761945Notes

Reaction equation

HRID 1761945 reaction equation
[C:1]([NH:4][C:5]1[C:6](=[O:17])[C:7]2[C:12]([C:13](=[O:16])[C:14]=1Cl)=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[CH2:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[O:17]=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13](=[O:16])[C:14]([N:28]2[CH2:29][CH2:30][N:25]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:26][CH2:27]2)=[C:5]1[NH:4][C:1](=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 72754Acetamide, N-(1,4-dihydro-3-chloro-1,4-dioxo-2-naphthyl)-HCID 759941-Benzylpiperazine

Product 1

HCID 2926585HCID 2926585, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 500 mg of 2-acetylamino-3chloro-1,4-naphthoquinone, 800 mg of N-benzylpiperazine and 40 ml of absolute ethanol was heated at reflux for 3 hours, then the solvent was removed. The remainder was passed through a small plug of silica gel and eluted with chloroform. The eluate was concentrated to a solid which was recrystallized from dichloromethane/hexane, giving 700 mg of the desired product, mp 153°-155° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customthe solvent was removed
  4. washeluted with chloroform
  5. concentrationThe eluate was concentrated to a solid which
  6. customwas recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-116ee083ef38411fa269eecef9a23d03
Source dataset
uspto-grants-1989_05
Patent number
US04829089

Reaction notes

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