2-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline → HCID 19419852, compound

HRID 1440701Notes

Reaction equation

HRID 1440701 reaction equation
[Cl:1][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>N1CCCCC1>[ClH:1].[N:12]1([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)[CH2:13][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

3

Reactant 1

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

Product 1

HCID 19419852HCID 19419852, compoundYield 170.4%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

A solution of 2-chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline (3.5 g) in piperidine (20 ml) was stirred under reflux, under nitrogen, for four hrs. The reaction mixture was quenched with dilute sodium bicarbonate solution (200 ml) and the aqueous suspension was extracted with chloroform. The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by high performance liquid chromatography (silica gel; 3:1 dichloromethane-ethyl acetate). The appropriate fractions were collected and concentrated. This residue was dissolved in ether and treated dropwise with a solution of hydrogen chloride/ether. The precipitate was collected and washed with ether to give 4.3 g (85%) of product, mp 260° C.

Workup

  1. temperatureunder reflux, under nitrogen, for four hrs
  2. customThe reaction mixture was quenched with dilute sodium bicarbonate solution (200 ml)
  3. extractionthe aqueous suspension was extracted with chloroform
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by high performance liquid chromatography (silica gel; 3:1 dichloromethane-ethyl acetate)
  7. customThe appropriate fractions were collected
  8. concentrationconcentrated
  9. dissolutionThis residue was dissolved in ether
  10. additiontreated dropwise with a solution of hydrogen chloride/ether
  11. customThe precipitate was collected
  12. washwashed with ether

Sources & evidence

ORD record
ord-a25e78466d294c3ca6cd2287ea1468be
Source dataset
uspto-grants-1996_03
Patent number
US05500423

Reaction notes

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