3-Amino-1-propanol → HCID 25070095, compound

HRID 1893439Notes

Reaction equation

HRID 1893439 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][N:14]=[C:7]1[C:6](Cl)=[N:5]2.[NH2:16][CH2:17][CH2:18][CH2:19][OH:20]>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][N:14]=[C:7]1[C:6]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])=[N:5]2

Participants

5

Reactant 2

HCID 90863-Amino-1-propanolHCID 59333351HCID 59333351, compound

Product 1

HCID 25070095HCID 25070095, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 7-bromo-4-chloro-imidazo[1,2-a]quinoxaline (2.75 g; 9.6 mmol; 1 eq) in anhydrous dioxane (421 mL), 3-aminopropanol (1.83 mL; 24.1 mmol; 2.5 eq) is added under argon atmosphere. After 17 hours of stirring under reflux, the reaction mixture is cooled to room temperature and diluted in ethyl acetate (250 mL). The organic phase is washed three times with a molar solution of sodium hydroxide (3×150 mL). The recombined water phases are extracted one more time with ethyl acetate (300 mL) and the combined organic phases dried over sodium sulfate and concentrated under vacuum. The resulting beige powder is further washed with ether (200 mL) to provide the title compound (2.70 g; 8.4 mmol; 89%) as a grey powder.

Workup

  1. temperatureunder reflux
  2. washThe organic phase is washed three times with a molar solution of sodium hydroxide (3×150 mL)
  3. extractionThe recombined water phases are extracted one more time with ethyl acetate (300 mL)
  4. dry with materialthe combined organic phases dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. washThe resulting beige powder is further washed with ether (200 mL)

Sources & evidence

ORD record
ord-6be6440eef6d4272b5193a5d77af1a97
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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