1-(4-Fluorophenyl)piperazine → HCID 13934781, compound

HRID 1761949Notes

Reaction equation

HRID 1761949 reaction equation
[C:1]([N:4]([C:8]1[C:9](=[O:20])[C:10]2[C:15]([C:16](=[O:19])[C:17]=1Cl)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[F:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1>C(O)C>[C:1]([N:4]([C:8]1[C:9](=[O:20])[C:10]2[C:15]([C:16](=[O:19])[C:17]=1[N:31]1[CH2:30][CH2:29][N:28]([C:25]3[CH:24]=[CH:23][C:22]([F:21])=[CH:27][CH:26]=3)[CH2:33][CH2:32]1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 752601-(4-Fluorophenyl)piperazineHCID 11716254HCID 11716254, compound

Product 1

HCID 13934781HCID 13934781, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.66 g of 2-[N,N-diacetylamino]-3-chloro-1,4-naphthoquinone and 1.441 g of 1-(4-fluorophenyl)-piperazine in 50 ml of ethanol was refluxed overnight, then evaporated in vacuo. The residue was dissolved in dichloromethane, filtered through silica gel and eluted with chloroform:methanol (100:2). The eluent was evaporated and the residue crystallized from dichloromethane/-hexane, giving 800 ml of the desired product, mp 149°-150° C.

Workup

  1. temperaturewas refluxed overnight
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. filtrationfiltered through silica gel
  5. washeluted with chloroform:methanol (100:2)
  6. customThe eluent was evaporated
  7. customthe residue crystallized from dichloromethane/-hexane

Sources & evidence

ORD record
ord-3f03de0f6cd848a9a53cb06a39fc1075
Source dataset
uspto-grants-1989_05
Patent number
US04829089

Reaction notes

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