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

HRID 1649222Notes

Reaction equation

HRID 1649222 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+].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1.CN(C=O)C>O>[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][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:28][CH:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 11630008HCID 11630008, compound

Product 1

HCID 132363455-[4-(4-Methoxybenzyl)-1-piperazinyl]-3,4-dihydrocarbostyrilYield 3.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.0 g of 5-(1-piperazinyl)-3,4-dihydrocarbostyril, 1.11 g of potassium carbonate, 760 mg of 4-methoxybenzyl chloride and 20 ml of DMF was stirred at 70°-80° C. for 4 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. Recrystallization from methanol gave 60 mg of 5-[4-(4-methoxybenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 194°-196° C., colorless needles.

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. customRecrystallization from methanol

Sources & evidence

ORD record
ord-8d040a85d93a49948cd8ec20593fa0cc
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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