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

HRID 1440706Notes

Reaction equation

HRID 1440706 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.[CH2:14]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([N:21]1[CH2:26][CH2:25][N:24]([C:2]2[N:12]3[C:13]4[C:8]([CH2:9][CH2:10][CH2:11]3)=[CH:7][CH:6]=[CH:5][C:4]=4[N:3]=2)[CH2:23][CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 759941-BenzylpiperazineHCID 152871052-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline

Product 1

HCID 194198375,6-Dihydro-2-(4-benzyl-1-piperazinyl)-4H-imidazo[4,5,1-ij]quinolineYield 70%

Procedure

A solution of 2-chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline (3.00 g) in 1-benzylpiperazine (10 ml) was stirred at 100° C., under nitrogen, for four hrs. The reaction mixture was quenched with dilute sodium bicarbonate solution (300 ml) and extracted with dichloromethane. 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; 25:1 dichloromethane-methanol). The appropriate fractions were collected and evaporated. The residue was recrystallized from ethyl acetate to give 3.6 g (70%) of product, mp 157°-158° C.

Workup

  1. customThe reaction mixture was quenched with dilute sodium bicarbonate solution (300 ml)
  2. extractionextracted with dichloromethane
  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; 25:1 dichloromethane-methanol)
  7. customThe appropriate fractions were collected
  8. customevaporated
  9. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6056e77850404251aabf14895d71d1d1
Source dataset
uspto-grants-1996_03
Patent number
US05500423

Reaction notes

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