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Dimethyl Sulfoxide → 5-[5-(4-Phenyl-1-piperazinyl)valeryl]-2-benzyloxy-benzamide

HRID 65208
Notes
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Reaction equation

HRID 65208 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:12]([CH:16]=1)[C:13]([NH2:15])=[O:14])=[O:7].[C:25]1([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+].CS(C)=O>O>[C:25]1([N:31]2[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]3[CH:9]=[CH:10][C:11]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[C:12]([CH:16]=3)[C:13]([NH2:15])=[O:14])=[O:7])[CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 70961-PhenylpiperazineHCID 10340Sodium CarbonateHCID 202339675-(5-Chlorovaleryl)-2-benzyloxy-benzamide

Product 1

HCID 202339515-[5-(4-Phenyl-1-piperazinyl)valeryl]-2-benzyloxy-benzamideYield 84.3%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2 g of 5-(5-chlorovaleryl)-2-benzyloxy-benzamide, 1 g of 1-phenylpiperazine, 0.6 g of sodium carbonate and 10 ml of dimethyl sulfoxide was heated at 90° C. for 6 hours while stirring. After the reaction was finished, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water saturated with sodium chloride, dried over anhydrous sodium sulfate and concentrated. The thus produced residue was dissolved in acetone and concentrated hydrochloric acid in an amount of 2 equivalents was added thereto to produce crystals. The crystals were filtered off to obtain 2.3 g of 5-[5-(4-phenyl-1-piperazinyl)valeryl]-2-benzyloxy-benzamide (yield: 73%).

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. concentrationconcentrated
  5. dissolutionThe thus produced residue was dissolved in acetone
  6. additionconcentrated hydrochloric acid in an amount of 2 equivalents was added
  7. customto produce crystals
  8. filtrationThe crystals were filtered off

Sources & evidence

ORD record
ord-cfbb51c4de9446b3ae8f6ac9ea57ff96
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04613598

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes