Hydrochloric Acid → HCID 21331806, compound

HRID 1390976Notes

Reaction equation

HRID 1390976 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C:16]1([CH3:36])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[CH2:24][CH2:23]1.Cl>C(O)C>[CH3:36][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[CH2:23][CH2:24][N:25]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([NH:35][C:2]3[C:11]4[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=4)[N:5]=[CH:4][CH:3]=3)=[CH:33][CH:34]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 676684-Chloro-7-(trifluoromethyl)quinolineHCID 21331819HCID 21331819, compound

Product 1

HCID 21331806HCID 21331806, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloro-7-trifluoromethyl quinoline (1 g, 0.00216 M), 4-(o-tolyl)-1-p-aminobenzylpiperazine (1.3 g, 0.0046 M) and 3 ml of ethanolic hydrogen chloride in 25 ml of ethanol is heated at reflux for 6 hours under nitrogen. The reaction mixture is quenched with ice water, neutralized with aqueous 10% aqueous sodium hydroxide solution and extracted with methylene chloride. The methylene chloride solution is washed with water, dried over anhydrous sodium sulfate and concentrated to a white solid which, after recyrstallization from ethyl acetate/Skellysolve®B, affords 1.9 g (92%) of white crystalline 4-[[4-[[4-(2-methylpenyl)-1-piperazinyl]methyl]phenyl]amino]-7-(trifluoromethyl)quinoline of melting point 208°-210° C.

Workup

  1. temperatureat reflux for 6 hours under nitrogen
  2. customThe reaction mixture is quenched with ice water
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride solution is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to a white solid which

Sources & evidence

ORD record
ord-3f7a9e82ec9b4bd58ba959b36cb43285
Source dataset
uspto-grants-1979_02
Patent number
US04140775

Reaction notes

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