Potassium Carbonate → HCID 54159860, compound

HRID 981865Notes

Reaction equation

HRID 981865 reaction equation
[N:1]1([C:6]([O:8][C:9]2[C:10]([F:20])=[CH:11][C:12]3[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=3[CH:19]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.I[CH2:22][CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[N:1]1([C:6]([O:8][C:9]2[C:10]([F:20])=[CH:11][C:12]3[O:17][CH2:16][C:15](=[O:18])[N:14]([CH2:22][CH2:23][CH3:24])[C:13]=3[CH:19]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 336431-IodopropaneHCID 20068406HCID 20068406, compound

Product 1

HCID 54159860HCID 54159860, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 0.70 g (0.0025 mole) of 7-fluoro-2H-1,4-benzoxazin-3(4H)-one-6-yl 1-pyrrolidinecarboxylate, 0.60 g (0.0036 mole) of 1-iodopropane, 1.1 g (0.0076 mole) of potassium carbonate, and 0.1 g (0.00038 mole) of 18-crown-6 in 50 mL of acetone was heated at reflux for five hours. The reaction mixture was cooled, filtered and the filtrate evaporated under reduced pressure leaving a residue. The residue was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure leaving a residue. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate-heptane (50:50), to yield 0.6 g of (7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-one-6-yl) 1-pyrrolidinecarboxylate as a solid 73°-75° C., Compound 4 of Table 1. The nmr ir spectra were consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for five hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure
  6. customleaving a residue
  7. extractionThe residue was extracted with ethyl acetate
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe filtrate evaporated under reduced pressure
  11. customleaving a residue
  12. customThe residue was purified by column chromatography on silica gel
  13. washeluting with ethyl acetate-heptane (50:50)

Sources & evidence

ORD record
ord-95b056660acb44d583fcb5a252ce8b42
Source dataset
uspto-grants-1991_02
Patent number
US04994104

Reaction notes

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