1-Phenylpiperazine → 5,6-Dihydro-2-(4-phenyl-1-piperazinyl)-4H-imidazo[4,5,1-ij]quinoline

HRID 1440704Notes

Reaction equation

HRID 1440704 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:14]1([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([N:20]2[CH2:25][CH2:24][N:23]([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)[CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 70961-PhenylpiperazineHCID 152871052-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline

Product 1

HCID 194198485,6-Dihydro-2-(4-phenyl-1-piperazinyl)-4H-imidazo[4,5,1-ij]quinolineYield 45%

Procedure

A solution of 2-chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline (3.00 g) in 1-phenylpiperazine (10 ml) was stirred at 100° C., under nitrogen, for five hrs. The reaction mixture was quenched with saturated sodium bicarbonate solution (200 ml) and extracted with chloroform. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was purified by high performance liquid chromatography (silica gel; 4:1 dichloromethane-ethyl acetate). The appropriate fractions were collected and evaporated. The residue was recrystallized from ethyl acetate to give 2.2 g (45%) of product, mp 168°-169° C.

Workup

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

Sources & evidence

ORD record
ord-5f438f16cb80427aaefa50111b70c43e
Source dataset
uspto-grants-1996_03
Patent number
US05500423

Reaction notes

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