1-(3-(Trifluoromethyl)phenyl)piperazine → 2-[4-[3-(Trifluoromethyl)phenyl]-1-piperazinyl]-5,6-dihydro-4H-imidazo [4,5,1-ij]quinoline

HRID 864648Notes

Reaction equation

HRID 864648 reaction equation
Cl[C:2]1[N:12]2[C:13]3[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=1.C(Cl)(Cl)Cl.[F:18][C:19]([F:33])([F:32])[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1>>[F:33][C:19]([F:18])([F:32])[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][N:29]([C:2]3[N:12]4[C:13]5[C:8]([CH2:9][CH2:10][CH2:11]4)=[CH:7][CH:6]=[CH:5][C:4]=5[N:3]=3)[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 6212ChloroformHCID 152871052-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline

Product 1

HCID 189819432-[4-[3-(Trifluoromethyl)phenyl]-1-piperazinyl]-5,6-dihydro-4H-imidazo [4,5,1-ij]quinolineYield 50%

Procedure

A solution of 2-chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline (3.00 g) in 1-[3-(trifluoromethyl)phenyl]piperazine (5 ml) was stirred at 110° C., under nitrogen. After four hrs, chloroform (50 ml) was added, and the solution was stirred under reflux overnight. The reaction mixture was quenched with dilute sodium bicarbonate solution (200 ml) and extracted with chloroform. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated. The residue was purified by high performance liquid chromatography (silica gel; 8:1 dichloromethane-ethyl acetate). The appropriate fractions were collected and evaporated. The residue was recrystallized from ethyl acetate to give 3.0 g (50%) of product, mp 158°-159° C.

Workup

  1. temperatureunder reflux overnight
  2. customThe reaction mixture was quenched with dilute sodium bicarbonate solution (200 ml)
  3. extractionextracted with chloroform
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated
  7. customThe residue was purified by high performance liquid chromatography (silica gel; 8:1 dichloromethane-ethyl acetate)
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7387bee953764e76bd40627ce8bef835
Source dataset
uspto-grants-1996_10
Patent number
US05563272

Reaction notes

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