Morpholine → HCID 13533247, compound

HRID 1730909Notes

Reaction equation

HRID 1730909 reaction equation
Br[CH:2]([CH2:18]C)[C:3]([C:5]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:17])[NH:10]2)=[O:4].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.O>[O:23]1[CH2:24][CH2:25][N:20]([CH:2]([CH3:18])[C:3]([C:5]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]3[C:6]=2[CH2:7][CH2:8][C:9](=[O:17])[NH:10]3)=[O:4])[CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 13533239HCID 13533239, compound

Product 1

HCID 13533247HCID 13533247, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

5 g of 5-(α-bromopropionyl)-8-hydroxy-3,4-dihydrocarbostyril (IV) was suspended in 30 ml of benzene, and 4.2 ml of morpholine (III) was added to the suspension followed by allowing the mixture to react for 4 hours while heating under refluxing. The reaction mixture was filtered and the filtrate was washed with water followed by concentration under reduced pressure to remove any remaining water. The resulting residue was dissolved in 50 ml of isopropanol, and the solution was adjusted to a pH of 2 - 3 with concentrated hydrochloric acid. The viscous precipitate formed upon ice-cooling was separated and dissolved in acetone by heating. After allowing the solution to cool, the precipitate formed was dissolved in 30 ml of water and adjusted to a pH of 7.5 - 8 with sodium bicarbonate. The precipitate formed upon ice-cooling was filtered and dissolved in 10 ml of a 47% aqueous hydrobromic acid followed by concentration under reduced pressure. The residue thus obtained was washed with 10 ml of ethanol and recrystallized from ethanol to obtain 2.6 g of white amorphous 5-(α-morpholinopropionyl)-8-hydroxy-3,4-dihydrocarbostyril (IIb) hydrobromide monohydrate having a melting point of 235° - 236° C (with decomposition).

Workup

  1. customto react for 4 hours
  2. temperaturewhile heating
  3. temperatureunder refluxing
  4. filtrationThe reaction mixture was filtered
  5. washthe filtrate was washed with water
  6. concentrationfollowed by concentration under reduced pressure
  7. customto remove any remaining water
  8. dissolutionThe resulting residue was dissolved in 50 ml of isopropanol
  9. customThe viscous precipitate formed upon ice-
  10. temperaturecooling
  11. customwas separated
  12. dissolutiondissolved in acetone
  13. temperatureby heating
  14. temperatureto cool
  15. customthe precipitate formed
  16. customThe precipitate formed upon ice-
  17. temperaturecooling
  18. filtrationwas filtered
  19. dissolutiondissolved in 10 ml of a 47% aqueous hydrobromic acid
  20. concentrationfollowed by concentration under reduced pressure
  21. customThe residue thus obtained
  22. washwas washed with 10 ml of ethanol
  23. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-522582ad9a5c49d99adc5c64dc2ca03f
Source dataset
uspto-grants-1976_11
Patent number
US03994901

Reaction notes

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