Sodium Bicarbonate → 1-{3-{Bis[4-(methoxymethoxy)phenyl]methyl}indol-2-ylcarbonyl}-4-(2-chlorophenyl)piperazine

HRID 442848Notes

Reaction equation

HRID 442848 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:22]=[CH:21][C:8]([CH:9](O)[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][O:18][CH3:19])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][N:33]([C:36]([C:38]2[NH:39][C:40]3[C:45]([CH:46]=2)=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:37])[CH2:32][CH2:31]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:22]=[CH:21][C:8]([CH:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][O:18][CH3:19])=[CH:12][CH:11]=2)[C:46]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[NH:39][C:38]=2[C:36]([N:33]2[CH2:32][CH2:31][N:30]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[Cl:23])[CH2:35][CH2:34]2)=[O:37])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 17877334HCID 17877334, compoundHCID 54082355HCID 54082355, compound

Product 1

HCID 158589011-{3-{Bis[4-(methoxymethoxy)phenyl]methyl}indol-2-ylcarbonyl}-4-(2-chlorophenyl)piperazineYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride-ether complex (0.36 ml, 2.94 mmol) was added dropwise at 0° C. to a solution of 4,4'-bis(methoxymethoxy)benzhydrol (8.96 g, 29.43 mmol) and 1-(2-chlorophenyl)-4-(indol-2-ylcarbonyl)piperazine (10.0 g, 29.43 mmol) in 200 ml of methylene chloride, followed by stirring at 0° C. to room temperature for 2 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 a crude product. The obtained crude product was recrystallized from ethanol to, give 15.1 g (yield: 82%) of the title compound.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto give a crude product
  6. customThe obtained crude product
  7. customwas recrystallized from ethanol to,

Sources & evidence

ORD record
ord-6a035043ba434d559b4d4ca58b09138a
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

Loading…