Water → AD 1308

HRID 1732295Notes

Reaction equation

HRID 1732295 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 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.0 g of 2-chloro-4-phenylquinoline and 2.7 g of 1-ethylpiperazine in 15 ml of toluene was heated under reflux for 10 hours. To the reaction mixture was added water and the resulting mixture was extracted with ethyl acetate. The extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel (25 g) using chloroform as an eluent. Fractions containing the title compound were pooled and concentrated to give the title compound (2.3 g, 87% ), m.p. 87°-88° C.

Workup

  1. temperatureunder reflux for 10 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe extracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica gel (25 g)
  6. additionFractions containing the title compound
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ac0adace0fa44d368ebebf59aadf57ac
Source dataset
uspto-grants-1980_12
Patent number
US04237135

Reaction notes

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