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Dimethyl Sulfoxide → 5-[4-(4-Aminobenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril dihydrochloride monohydrate

HRID 1649226
Notes
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Reaction equation

HRID 1649226 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH2:9][CH2:10][C:11](=[O:17])[NH:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[NH2:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][Cl:34])=[CH:31][CH:30]=1>O>[OH2:17].[ClH:34].[ClH:34].[NH2:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:8]=3[CH2:9][CH2:10][C:11](=[O:17])[NH:12]4)[CH2:2][CH2:3]2)=[CH:31][CH:30]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 113209864-ChloromethylanilineHCID 11630008HCID 11630008, compound

Product 1

HCID 204805705-[4-(4-Aminobenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril dihydrochloride monohydrateYield 40.8%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1.2 g of 5-(1-piperazinyl)-3,4-dihydrocarbostyril, 1.17 g of potassium carbonate and 20 ml of dimethyl sulfoxide was added 650 mg of 4-aminobenzyl chloride and the mixture was stirred at 80° C. for 2.5 hours. The reaction mixture was poured into a large amount of water and extracted with chloroform. After washing with water, the extract was dried over anhydrous sodium sulfate. Chloroform was distilled off and the residue was purified through silica gel column chromatography. After conversion to hydrochloric acid salt with methanol-hydrochloric acid, the product was recrystallized from methanol-ether to give 0.4 g of 5-[4-(4-aminobenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril dihydrochloride monohydrate, m.p. 224°-227° C. (decomp.), yellow granules.

Workup

  1. extractionextracted with chloroform
  2. washAfter washing with water
  3. dry with materialthe extract was dried over anhydrous sodium sulfate
  4. distillationChloroform was distilled off
  5. customthe residue was purified through silica gel column chromatography
  6. customAfter conversion to hydrochloric acid salt with methanol-hydrochloric acid, the product was recrystallized from methanol-ether

Sources & evidence

ORD record
ord-d29db4f53c1a4a4f82307da6de3e000a
Source dataset
uspto-grants-1983_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04415572

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes