Dimethyl Sulfoxide → 5-[5-[4-(2-Methoxyphenyl)-1-piperazinyl]valeryl]-2-methoxy-benzenesulfonamide dihydrochloride

HRID 65206

Reaction equation

HRID 65206 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([O:18][CH3:19])=[C:12]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:13]=1)=[O:7].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[Na+].[Na+].CS(C)=O>O>[ClH:1].[ClH:1].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]2[CH:9]=[CH:10][C:11]([O:18][CH3:19])=[C:12]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:13]=2)=[O:7])[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 13461-(2-Methoxyphenyl)piperazineHCID 10340Sodium CarbonateHCID 218869805-(5-Chloropentanoyl)-2-methoxybenzenesulfonamide

Product 1

HCID 202339475-[5-[4-(2-Methoxyphenyl)-1-piperazinyl]valeryl]-2-methoxy-benzenesulfonamide dihydrochlorideYield 123.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2.6 g of 5-(5-chlorovaleryl)-2-methoxy-benzenesulfonamide, 1.8 g of 1-(2-methoxyphenyl)piperazine, 1 g of sodium carbonate and 20 ml of dimethyl sulfoxide was stirred at 90° C. for 3 hours. After the reaction was finished, water was added to the reaction mixture and then the mixture was extracted with ethyl acetate. The extract was washed with water saturated with sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled away and the residue was dissolved in acetone followed by adding concentrated hydrochloric acid in required amount to produce crystals. The thus-produced crystals were recrystallized from methanol to obtain 2.8 g of the titled compound (yield: 61%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water saturated with sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away
  5. dissolutionthe residue was dissolved in acetone
  6. additionby adding concentrated hydrochloric acid in required amount
  7. customto produce crystals
  8. customThe thus-produced crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-851a04a25f894117b3242313f905eb84
Source dataset
uspto-grants-1986_09
Patent number
US04613598

Linked notes

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