Morpholine → HCID 57677759, compound

HRID 492751Notes

Reaction equation

HRID 492751 reaction equation
C1(O[C:8](=[O:26])[NH:9][C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=3)[CH:13]=[CH:12][N:11]=2)C=CC=CC=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>O1CCCC1>[N+:23]([C:20]1[CH:19]=[CH:18][C:17]([O:16][C:14]2[CH:13]=[CH:12][N:11]=[C:10]([NH:9][C:8]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[O:26])[CH:15]=2)=[CH:22][CH:21]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 8083Morpholine2×HCID 57677544[4-(4-Nitrophenoxy)pyridin-2-yl]carbamic acid phenyl ester

Product 1

HCID 57677759HCID 57677759, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[4-(4-Nitrophenoxy)pyridin-2-yl]carbamic acid phenyl ester (250 mg) was dissolved in tetrahydrofuran (7 ml) under a nitrogen atmosphere, and then morpholine (0.187 ml) was added thereto. The reaction mixture was stirred overnight at room temperature. To the reaction mixture was further added morpholine (0.187 ml), followed by stirring for 2 hrs and 15 min. The reaction mixture was warmed up to 50° C., followed by stirring for 1 hr. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of ammonium chloride. The organic layer was washed with a saturated aqueous solution of ammonium chloride, water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1 to 1:5). Fractions containing the target compound were concentrated under a reduced pressure to give a residue, which was then dried in vacuum to provide the titled compound (152 mg, 61.9%) as a brown solid.

Workup

  1. stirringby stirring for 2 hrs and 15 min
  2. temperatureThe reaction mixture was warmed up to 50° C.
  3. stirringby stirring for 1 hr
  4. customThe reaction mixture was partitioned between ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride, water and brine in this order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under a reduced pressure
  8. customto give a residue, which
  9. customwas then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1 to 1:5)
  10. additionFractions containing the target compound
  11. concentrationwere concentrated under a reduced pressure
  12. customto give a residue, which
  13. customwas then dried in vacuum

Sources & evidence

ORD record
ord-51dd5f3356e64658b8138d0df8cfeae4
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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