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

HRID 1440699Notes

Reaction equation

HRID 1440699 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.[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C(=O)(O)[O-].[Na+].O>[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([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)[CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 152871052-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline

Product 1

HCID 153457165,6-Dihydro-2-(4-methyl-1-piperazinyl)-4H-imidazo[4,5,1-ij]quinolineYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline (4.30 g) in 20 ml of N-methylpiperazine (18.06 g) was heated under reflux, under nitrogen, with stirring. After 30 mins, the solution was diluted with sodium bicarbonate solution (100 ml) and water (200 ml). The aqueous solution was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by high performance liquid chromatography (silica gel; methanol). The appropriate fractions were collected and evaporated. The residue was crystallized from ether-petroleum ether to give 4.0 g (70%) of product, mp 112°-113° C.

Workup

  1. temperatureunder reflux, under nitrogen
  2. extractionThe aqueous solution was extracted with chloroform
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by high performance liquid chromatography (silica gel; methanol)
  6. customThe appropriate fractions were collected
  7. customevaporated
  8. customThe residue was crystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-15c36759bb614c2987caf405cd69131a
Source dataset
uspto-grants-1996_03
Patent number
US05500423

Reaction notes

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