Morpholine → HCID 15345717, compound

HRID 1440700Notes

Reaction equation

HRID 1440700 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-5f594a5bb06d439696d24f3bd02a0d0e
Source dataset
uspto-grants-1996_03
Patent number
US05500423

Reaction notes

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