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

HRID 1440707Notes

Reaction equation

HRID 1440707 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-b705b7855bc3450e819d34e7c0119cd8
Source dataset
uspto-grants-1996_03
Patent number
US05500423

Reaction notes

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