Dimethylformamide → 5-[4-(3,4-Dimethoxybenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril dihydrochloride

HRID 1649223Notes

Reaction equation

HRID 1649223 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.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:34][Cl:35]>O>[ClH:35].[ClH:35].[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:34][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

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 81740Veratryl chlorideHCID 11630008HCID 11630008, compound

Product 1

HCID 204805935-[4-(3,4-Dimethoxybenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril dihydrochlorideYield 58.4%

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 858 mg of 3,4-dimethoxybenzyl chloride and the mixture was stirred at 70°-80° C. for 2 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. The residue was converted to hydrochloric acid salt to give 610 mg of 5-[4-(3,4-dimethoxybenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril dihydrochloride, m.p. 270°-272.5° C. (decomp.).

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

Sources & evidence

ORD record
ord-d7ad9643f748485eaee173de2e81b7b1
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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