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

HRID 442849
Notes
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Reaction equation

HRID 442849 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:38][CH:37]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[CH2:25][CH2:24]2)=[O:22])=[CH:7][CH:6]=1.[H-].[Na+].Cl.[CH3:49][N:50]([CH3:54])[CH2:51][CH2:52]Cl.[Cl-].[NH4+]>CN(C)C=O.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([C:36]2[CH:37]=[CH:38][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:40][CH:41]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:52][CH2:51][N:50]([CH3:54])[CH3:49])[C:13]=2[C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[CH2:25][CH2:24]2)=[O:22])=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 158589011-{3-{Bis[4-(methoxymethoxy)phenyl]methyl}indol-2-ylcarbonyl}-4-(2-chlorophenyl)piperazine

Product 1

HCID 701465951-{3-{Bis[4-(methoxymethoxy)phenyl]methyl}-1-(2-dimethylaminoethyl)indol-2-ylcarbonyl}-4-(2-chlorophenyl)-piperazine
Yield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Compound 1 (2.0 g, 3.19 mmol) obtained in Example 1 in 30 ml of N,N-dimethylformamide was portionwise added sodium hydride (60% in oil, 270 mg, 6.71 mmol) with stirring at 0° C., and 2-dimethylaminoethylchloride hydrochloride (460 mg, 3.19 mmol) was added thereto, followed by heating to 80° C. and then stirring for one hour. A saturated aqueous solution of ammonium chloride was added to the reaction solution for neutralization, and water was added thereto followed by extraction with ethyl acetate. The resulting organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give 2.9 g of a crude product. The obtained crude product was purified with silica gel column chromatography (ethyl acetate/hexane=1/1-ethyl acetate alone) to give 2.1 g (yield: 94%) of the title compound.

Workup

  1. temperatureby heating to 80° C.
  2. stirringstirring for one hour
  3. additionwas added
  4. extractionthereto followed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto give 2.9 g of a crude product
  9. customThe obtained crude product
  10. customwas purified with silica gel column chromatography (ethyl acetate/hexane=1/1-ethyl acetate alone)

Sources & evidence

ORD record
ord-6eecc990e763474fa5080fd0b25b37a3
Source dataset
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05891902

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes