Water → AD 1308

HRID 653404Notes

Reaction equation

HRID 653404 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.[CH2:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[CH3:19].O>C1(C)C=CC=CC=1>[CH2:18]([N:20]1[CH2:25][CH2:24][N:23]([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)[CH2:22][CH2:21]1)[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 791961-EthylpiperazineHCID 23066872-Chloro-4-phenylquinoline

Product 1

HCID 175033AD 1308Yield 86.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-chloro-4-phenylquinoline (2.0 g) and 1-ethylpiperazine (2.7 g) in toluene (15 ml) is heated under reflux for 10 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 (25 g) using chloroform as an eluent. Fractions containing the title compound are pooled and concentrated to give the title compound (2.3 g).

Workup

  1. temperatureunder reflux for 10 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 (25 g)
  6. additionFractions containing the title compound
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fcdbce7b3243487a95c98c789e4f2d1d
Source dataset
uspto-grants-1987_06
Patent number
US04677107

Reaction notes

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