Methanesulfonic Acid → HCID 15858911, compound

HRID 442858Notes

Reaction equation

HRID 442858 reaction equation
C(O[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=O)C.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][N:28]([C:31]([C:33]2[NH:34][C:35]3[C:40]([CH:41]=2)=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])[CH2:27][CH2:26]1.CS(O)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][N:28]([C:31]([C:33]2[NH:34][C:35]3[C:40]([C:41]=2[CH:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 274281Diphenylmethyl acetateHCID 516892Sodium BicarbonateHCID 17877334HCID 17877334, compound

Product 1

HCID 15858911HCID 15858911, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Benzhydryl acetate (2.2 g, 9.71 mmol) and 2-[4-(2-chlorophenyl)piperazinylcarbonyl]indole (3.0 g, 8.83 mmol) were dissolved in a mixed solvent of methylene chloride (50 ml) and chloroform (50 ml), and methanesulfonic acid (1.72 ml, 26.5 mmol) was added thereto, followed by stirring at room temperature for 3 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution for neutralization followed by extraction with chloroform. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give 6.5 g of a crude product. The obtained crude product was washed with ethanol (60 ml) under heating to give 4.0 g (yield: 89%) of the title compound.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with chloroform
  3. washThe resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto give 6.5 g of a crude product
  7. customThe obtained crude product
  8. washwas washed with ethanol (60 ml)
  9. temperatureunder heating

Sources & evidence

ORD record
ord-657c9ab476994acc9cbf9d24577af1e2
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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