Sodium Bicarbonate → 3-(Bis[4-(methoxymethoxy)phenyl]methyl)-2-[4-(2-chlorophenyl)piperazinylsulfonyl]indole

HRID 442865Notes

Reaction equation

HRID 442865 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]1.[CH3:26][O:27][CH2:28][O:29][C:30]1[CH:47]=[CH:46][C:33]([CH:34](O)[C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][O:43][CH3:44])=[CH:37][CH:36]=2)=[CH:32][CH:31]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:44][O:43][CH2:42][O:41][C:38]1[CH:37]=[CH:36][C:35]([CH:34]([C:33]2[CH:46]=[CH:47][C:30]([O:29][CH2:28][O:27][CH3:26])=[CH:31][CH:32]=2)[C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[S:14]([N:11]2[CH2:10][CH2:9][N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH2:13][CH2:12]2)(=[O:16])=[O:15])=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 54082355HCID 54082355, compound2×HCID 675955552-[4-(2-Chlorophenyl)piperazinylsulfonyl]indole

Product 1

HCID 676918923-(Bis[4-(methoxymethoxy)phenyl]methyl)-2-[4-(2-chlorophenyl)piperazinylsulfonyl]indoleYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Boron trifluoride-ether complex (0.04 ml, 0.32 mmol) was added to a solution of 2-[4-(2-chlorophenyl)piperazinylsulfonyl]indole (1.2 g, 3.19 mmol) in 15 ml of methylene chloride, and a solution of 4,4'-bis(methoxymethoxy)benzhydrol (991 mg, 3.26 mmol) in 10 ml of methylene chloride was added thereto, followed by stirring at room temperature for 20 hours. Then, a solution of 4,4'-bis(methoxymethoxy)benzhydrol (490 mg, 1.60 mmol) in 10 ml of methylene chloride was further added to the reaction mixture to complete the reaction. 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 a crude product. The obtained crude product was crystallized from diisopropyl ether/hexane to give 1.9 g (yield: 90%) of the title compound.

Workup

  1. customthe reaction
  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 a crude product
  7. customThe obtained crude product
  8. customwas crystallized from diisopropyl ether/hexane

Sources & evidence

ORD record
ord-7ff96bf8c0dc4965a43d63583a2d5c68
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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