Dipropylamine → HCID 19752239, compound

HRID 483336Notes

Reaction equation

HRID 483336 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13]Br)=[CH:11][C:6]=2[O:5][CH2:4][C:3]1=[O:15].[CH2:16]([NH:19][CH2:20][CH2:21][CH3:22])[CH2:17][CH3:18]>O1CCOCC1>[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13][N:19]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:17][CH3:18])=[CH:11][C:6]=2[O:5][CH2:4][C:3]1=[O:15]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 14995353HCID 14995353, compound

Product 1

HCID 19752239HCID 19752239, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5.4 g of 4-methyl-7-(2-bromoethyl)2,3-dihydro 3-oxo 1,4-benzoxazine, dissolved beforehand in 120 cm3 of dioxane and 6 cm3 of (0.044 mol) of dipropyl-amine, are introduced into a 250 cm3 round-necked flask equipped with a reflux condendser. The mixture is heated to reflux with magnetic stirring for 4 days. After cooling, the reaction mixture is filtered and the filtrate is then evaporated on a water bath under vacuum. The residue is ground with distilled water and extracted with ethyl acetate. The organic phase is recovered and evaporated to dryness and the residue is taken up with 5% HCl solution. The acidic aqueous phase is washed with ethyl acetate and then alkalinized with 10% sodium hydroxide solution. It is extracted with ethyl acetate and the organic phase is washed with distilled water and then dried over potassium carbonate. The solvent is evaporated off on a water bath under vacuum. The residue is taken up in absolute ethanol, a stream of gaseous HCl is bubbled through and the mixture is then evaporated to dryness on a water bath under vacuum. The residue is ground in toluene or ether, then drained and dried. The product is recrystallized in anhydrous acetone.

Workup

  1. customequipped with a reflux condendser
  2. temperatureThe mixture is heated
  3. temperatureto reflux
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture is filtered
  6. customthe filtrate is then evaporated on a water bath under vacuum
  7. extractionextracted with ethyl acetate
  8. customThe organic phase is recovered
  9. customevaporated to dryness
  10. washThe acidic aqueous phase is washed with ethyl acetate
  11. extractionIt is extracted with ethyl acetate
  12. washthe organic phase is washed with distilled water
  13. dry with materialdried over potassium carbonate
  14. customThe solvent is evaporated off on a water bath under vacuum
  15. customa stream of gaseous HCl is bubbled through and the mixture
  16. customis then evaporated to dryness on a water bath under vacuum
  17. customdried
  18. customThe product is recrystallized in anhydrous acetone

Sources & evidence

ORD record
ord-3fc699705b3a45a9a1aeb7731ad9c2d4
Source dataset
uspto-grants-1993_07
Patent number
US05225409

Reaction notes

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