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Dimethylformamide → 5-[4-(3,4-Dichlorobenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril monohydrochloride monohydrate

HRID 1649225
Notes
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Reaction equation

HRID 1649225 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+].CN(C=O)C.[Cl:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:33]Cl>O>[OH2:17].[ClH:29].[Cl:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:33][N:4]1[CH2:5][CH2:6][N: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)[CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 76093,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 11630008HCID 11630008, compound

Product 1

HCID 204805885-[4-(3,4-Dichlorobenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril monohydrochloride monohydrateYield 16.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 DMF was added 895 mg of 3,4-dichlorobenzyl chloride and the mixture was stirred at 60°-70° C. for 3 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 to give 0.17 g of 5-[4-(3,4-dichlorobenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril monohydrochloride monohydrate, m.p. 298.5°-300° C. (decomp.), colorless granules.

Workup

  1. extractionextracted with chloroform
  2. washAfter washing with water the extract
  3. dry with materialwas 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

Sources & evidence

ORD record
ord-476273bcdc8f475f916eda529d7f7259
Source dataset
uspto-grants-1983_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04415572

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes