Water → 2-(1-Piperazinyl)-4-phenylquinolone

HRID 653405

Reaction equation

HRID 653405 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.O>C1(C)C=CC=CC=1>[N:18]1([C:2]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 23066872-Chloro-4-phenylquinoline

Product 1

HCID 1662802-(1-Piperazinyl)-4-phenylquinoloneYield 91.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-chloro-4-phenylquinoline (4.0 g) and anhydrous piperazine (8.0 g) in toluene (4 ml) is heated under reflux for 5 hours. To the reaction mixture is added water and the resulting mixture is extracted with ethyl acetate. The extracts are dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel (40 g) using chloroform as an eluent. Fractions containing the title compound are pooled and concentrated to give the title compound (4.4 g), m.p. 133°-134° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. extractionthe resulting mixture is extracted with ethyl acetate
  3. dry with materialThe extracts are dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel (40 g)
  6. additionFractions containing the title compound
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0fab2c8e58474efeb2d1022ba0ffa8ac
Source dataset
uspto-grants-1987_06
Patent number
US04677107

Linked notes

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