Water → HCID 19085578, compound

HRID 962761Notes

Reaction equation

HRID 962761 reaction equation
Br[CH2:2][CH2:3][CH:4]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[O:5][C:6]1[CH:30]=[CH:29][C:9]([C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:13]=2)=[O:11])=[CH:8][CH:7]=1.[CH3:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:31]1([CH:4]([O:5][C:6]2[CH:30]=[CH:29][C:9]([C:10]([C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:13]=3)=[O:11])=[CH:8][CH:7]=2)[CH2:3][CH2:2][N:48]2[CH2:47][CH2:46][N:45]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=3[O:38][CH3:37])[CH2:50][CH2:49]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13461-(2-Methoxyphenyl)piperazineHCID 11430Potassium CarbonateHCID 19085566HCID 19085566, compound

Product 1

HCID 19085578HCID 19085578, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-{3-[4-(3-bromo-1-phenylpropoxy)benzoyl]indol-1-yl}butanoate (1.97 g) obtained in Step 2 was dissolved in N,N-dimethylformamide (20 ml). 1-(2-Methoxyphenyl) piperazine (0.83 g) and potassium carbonate (0.75 g) were added to the resultant solution and stirred overnight at 60° C. After cooling, water was added to the reaction mixture, followed by extraction with ethyl acetate. The resultant extract was washed with brine and then dried. The solvent was distilled off. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), obtaining 1.95 g of ethyl 4-{3-{4-{1-phenyl-3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate as a colorless oily substance.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. extractionThe resultant extract
  4. washwas washed with brine
  5. customdried
  6. distillationThe solvent was distilled off
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-cbc870b02e0b43ceb3b3128384b3159a
Source dataset
uspto-grants-1998_06
Patent number
US05760040

Reaction notes

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