Morpholine → HCID 15345717, compound

HRID 864641Notes

Reaction equation

HRID 864641 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.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C(=O)(O)[O-].[Na+].O>[N:14]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)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 152871052-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline

Product 1

HCID 15345717HCID 15345717, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-chloro-5,6-dihydro-4H-imidazo [4,5,1-ij]quinoline (2.50 g) in morpholine (15 ml) was heated under reflux, under nitrogen, with stirring. After one hr, the solution was diluted with sodium bicarbonate solution (100 ml) and water (100 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; ethyl acetate). The appropriate fractions were collected and concentrated. The residue was crystallized from ether to give 2.1 g (67%) of product, mp 93°-94° 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; ethyl acetate)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated
  8. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-c2f3a403343347d98df2daf4254a1d07
Source dataset
uspto-grants-1996_10
Patent number
US05563272

Reaction notes

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