Hydrochloric Acid → HCID 21331814, compound

HRID 1390988Notes

Reaction equation

HRID 1390988 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.[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH2:19][CH2:18]1.Cl>C(O)C>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH:30][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:26][CH:25]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 676684-Chloro-7-(trifluoromethyl)quinolineHCID 31539964-((4-Methylpiperazin-1-yl)methyl)aniline

Product 1

HCID 21331814HCID 21331814, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloro-7-trifluoromethylquinoline (400 mg, 0.0018 M), 1-methyl-4-[(4-aminophenyl)methyl]piperazine (400 mg, 0.0019 M) and 1.4 ml of ethanolic hydrogen chloride in 10 ml of ethanol is heated to reflux, under nitrogen for 15 minutes. The reaction mixture is quenched with ice, neutralized with aqueous 10% sodium hydroxide and extracted with methylene chloride. The methylene chloride solution is washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to a white solid. This solid, after recrystallization from ethyl acetate, gives 250 mg (32%) of white crystalline 4-[[4-[(4-methyl-1-piperazinyl)methyl]phenyl]amino]-7-(trifluoromethyl)quioline of melting point 218°-220° C.

Workup

  1. temperatureto reflux, under nitrogen for 15 minutes
  2. customThe reaction mixture is quenched with ice
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride solution is washed with water, saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to a white solid
  7. customThis solid, after recrystallization from ethyl acetate
  8. customgives 250 mg (32%) of white crystalline 4-[[4-[(4-methyl-1-piperazinyl)methyl]phenyl]amino]-7-(trifluoromethyl)quioline of melting point 218°-220° C.

Sources & evidence

ORD record
ord-36f26b2bc4964eac92877372edbb59b7
Source dataset
uspto-grants-1979_02
Patent number
US04140775

Reaction notes

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