m-Chloroperbenzoic acid → HCID 11639106, compound

HRID 2224692Notes

Reaction equation

HRID 2224692 reaction equation
ClC1C=CC=[C:4]([C:8]([O:10]O)=[O:9])C=1.[CH2:12]([NH:19][CH2:20][CH2:21][C:22]1[CH:37]=[CH:36][C:25]([O:26][C:27]2[CH:32]=[CH:31][C:30](C(=O)C)=[CH:29][CH:28]=2)=[CH:24][CH:23]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl.ClCCl>[CH2:12]([NH:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:26][C:27]2[CH:28]=[CH:29][C:30]([O:10][C:8](=[O:9])[CH3:4])=[CH:31][CH:32]=2)=[CH:36][CH:37]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59717855HCID 59717855, compound

Product 1

HCID 11639106HCID 11639106, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Metachloroperbenzoic acid (0.23 g) was added to a solution of 1-{4-[4-(2-benzylamino-ethyl)-phenoxy]-phenyl}-ethanone (0.36 g) in chloroform (25 mL) while stirring at room temperature. Stirring was continued overnight then the reaction was diluted with dichloromethane, washed with saturated aqueous sodium thiosulfate, dried over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator. The residue was diluted with methanol (5 mL) and saturated aqueous sodium bicarbonate (5 mL) then stirred overnight at room temperature. The methanol was removed on a rotary evaporator and the pH of the residue was adjusted to 7-8 then extracted with dichloromethane (3×30 mL). The combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield 0.4 g of crude product, which was purified by flash column chromatography on silica gel eluting with ethanol in dichloromethane to yield Acetic acid 4-[4-(2-benzylamino-ethyl)-phenoxy]-phenyl ester (117 mg), 1H NMR (CDCl3, 300.00 MHz): 8.01-7.93 (m, 2H), 7.42-7.21 (m, 7H), 7.06-6.97 (m, 4H), 3.87 (s, 2H), 3.02-2.94 (m, 4H), 2.61 (s, 3H); m/z=361.85(M+1).

Workup

  1. stirringStirring
  2. washwashed with saturated aqueous sodium thiosulfate
  3. dry with materialdried over sodium chloride/magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. additionThe residue was diluted with methanol (5 mL) and saturated aqueous sodium bicarbonate (5 mL)
  7. stirringthen stirred overnight at room temperature
  8. customThe methanol was removed on a rotary evaporator
  9. extractionthen extracted with dichloromethane (3×30 mL)
  10. dry with materialThe combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated on a rotary evaporator
  13. customto yield 0.4 g of crude product, which
  14. customwas purified by flash column chromatography on silica gel eluting with ethanol in dichloromethane

Sources & evidence

ORD record
ord-52006f0dea5247a2892048ed7a63212f
Source dataset
uspto-grants-2008_05
Patent number
US07378448B2

Reaction notes

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