m-Chloroperbenzoic acid → 4-oxido-4-(2-{[1-oxo-3-phenyl-2-(pyridin-3-yl)-1H-inden-6-yl]oxy}ethyl)morpholin-4-ium

HRID 331291Notes

Reaction equation

HRID 331291 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[C:15]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:16]3=[O:19])=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:40])C=1>C(Cl)Cl.CCOC(C)=O>[O-:40][N+:4]1([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[C:15]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:16]3=[O:19])=[CH:12][CH:11]=2)[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 509405096-(2-morpholinoethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one

Product 1

HCID 866698614-oxido-4-(2-{[1-oxo-3-phenyl-2-(pyridin-3-yl)-1H-inden-6-yl]oxy}ethyl)morpholin-4-iumYield 26.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(2-morpholinoethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one (100 mg, 0.24 mmol) obtained in Step 7 of Example 1 in CH2Cl2 (2 mL) at 10° C. was added MCPBA (21 mg, 1 eq). The mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with EtOAc and washed with sat. NaHCO3, H2O, and brine. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (MC/MeOH/NH4OH=92:7:1) to afford the title compound (14 mg, 13%).

Workup

  1. washwashed with sat. NaHCO3, H2O, and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (MC/MeOH/NH4OH=92:7:1)

Sources & evidence

ORD record
ord-0f59250d38bf4a6981760ae83744cea1
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

Loading…