1-(2-Methoxyphenyl)piperazine → Ethyl 4-{3-{4-(4-methylphenylmethoxy)-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate

HRID 962769

Reaction equation

HRID 962769 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:34]=[CH:33][C:13]([C:14]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]([CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:17]=3)=[O:15])=[CH:12][C:11]=2[O:35][CH2:36][CH2:37][CH2:38]Cl)=[CH:4][CH:3]=1.[CH3:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:34]=[CH:33][C:13]([C:14]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]([CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:17]=3)=[O:15])=[CH:12][C:11]=2[O:35][CH2:36][CH2:37][CH2:38][N:51]2[CH2:50][CH2:49][N:48]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=3[O:41][CH3:40])[CH2:53][CH2:52]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 19085526Ethyl 4-{3-[4-(4-methylphenylmethoxy)-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoate

Product 1

HCID 19085533Ethyl 4-{3-{4-(4-methylphenylmethoxy)-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoateYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-{3-[4-(4-methylphenylmethoxy)-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoate (2.59 g) obtained in Step 2 was dissolved in N,N-dimethylformamide (30 ml). 1-(2-Methoxyphenyl)piperazine (1.36 g), potassium carbonate (0.85 g), and potassium iodide (1.02 g) were added to the resultant solution and stirred overnight at 60° C. The reaction mixture was poured into water and extracted 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=1:2), obtaining 2.47 g of ethyl 4-{3-{4-(4-methylphenylmethoxy)-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate as a colorless oily substance.

Workup

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

Sources & evidence

ORD record
ord-9a51cf912e8c45a687e1cf1e79deb12a
Source dataset
uspto-grants-1998_06
Patent number
US05760040

Linked notes

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