1-(2-Methoxyphenyl)piperazine → HCID 19085540, compound

HRID 962765Notes

Reaction equation

HRID 962765 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:35]=[CH:34][C:13]([C:14]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]([S:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:27])=[O:26])[CH:17]=3)=[O:15])=[CH:12][C:11]=2[O:36][CH2:37][CH2:38][CH2:39]Cl)=[CH:4][CH:3]=1.[CH3:41][O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]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:35]=[CH:34][C:13]([C:14]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]([S:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:27])=[O:26])[CH:17]=3)=[O:15])=[CH:12][C:11]=2[O:36][CH2:37][CH2:38][CH2:39][N:52]2[CH2:51][CH2:50][N:49]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=3[O:42][CH3:41])[CH2:54][CH2:53]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 19085541HCID 19085541, compound

Product 1

HCID 19085540HCID 19085540, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3-[4-(4-Methylphenylmethoxy)-3-(3-chloropropoxy) benzoyl]-1-(phenylsulfonyl)indole (0.44 g) obtained in Step 2 was dissolved in N,N-dimethylformamide (5 ml). 1-(2-Methoxyphenyl)piperazine (0.20 g), potassium carbonate (0.14 g), and potassium iodide (0.38 g) were added to the resultant solution and the mixture was stirred overnight at 60° C. 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=1:3), obtaining 0.29 g of 3-{4-(4-methylphenylmethoxy)-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}-1-(phenylsulfonyl)indole (0.29 g) as a light yellow oily substance.

Workup

  1. extractionfollowed by extraction 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=1:3)

Sources & evidence

ORD record
ord-dd4b11bf879b4438ad57a3db452c4bc7
Source dataset
uspto-grants-1998_06
Patent number
US05760040

Reaction notes

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