Triphenylphosphine → 6-(2-morpholine-4-yl ethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amide

HRID 17886

Reaction equation

HRID 17886 reaction equation
[CH:1]([NH-:4])([CH3:3])[CH3:2].[OH:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:11]([C:16]([O-:18])=[O:17])[C:12]2=[O:15])=[CH:8][CH:7]=1.O[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.C1C=CC=CC=1>[CH:1]([NH-:4])([CH3:3])[CH3:2].[N:28]1([CH2:27][CH2:26][O:5][C:6]2[CH:14]=[C:13]3[C:9]([C:10]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[C:11]([C:16]([O-:18])=[O:17])[C:12]3=[O:15])=[CH:8][CH:7]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178458041HCID 178458041, compound

Product 1

HCID 866140296-(2-morpholine-4-yl ethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amideYield 99%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amide (7.0 g, 22.78 mmol) was dissolved in tetrahydrofuran:benzene (150 ml:50 ml). Then, hydroxyethylmorpholine (3.59 g, 27.33 mmol) and triphenyl phosphine (7.17 g, 27.33 mmol) were added thereto. When the temperature was adjusted to 0° C., diisopropyl azodicarboxylate (5.53 g, 27.33 mmol) was added dropwise to the mixture followed by stirring for 2 hours at room temperature. The mixture was washed with brine and extracted with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 6-(2-morpholine-4-yl ethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amide (9.5 g, yield 99%).

Workup

  1. customwas adjusted to 0° C.
  2. washThe mixture was washed with brine
  3. extractionextracted with ethyl acetate
  4. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-5da6139b69b8451d84463995d522f076
Source dataset
uspto-grants-2010_06
Patent number
US07741323B2

Linked notes

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