1,3-Benzodioxole, 5-(chloromethyl)- → HCID 20480565, compound

HRID 1649230Notes

Reaction equation

HRID 1649230 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[K+].[CH2:23]1[O:33][C:32]2[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][C:25]=2[O:24]1>CN(C=O)C>[CH2:23]1[O:33][C:32]2[CH:31]=[CH:30][C:27]([CH2:28][N:4]3[CH2:5][CH2:6][N:1]([C:7]4[CH:8]=[C:9]5[C:14](=[CH:15][CH:16]=4)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]5)[CH2:2][CH2:3]3)=[CH:26][C:25]=2[O:24]1

Participants

5

Reactant 3

HCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 516893Potassium BicarbonateHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 20480565HCID 20480565, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1.2 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril, 1.17 g of potassium bicarbonate and 20 ml of DMF was added 785 mg of 3,4-methylenedioxybenzyl chloride and the mixture was stirred at 80°-90° C. for 3.5 hours. The reaction mixture was poured into a large amount of saturated saline solution 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 to give 0.2 g of 6-[4-(3,4-methylenedioxybenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril.

Workup

  1. additionThe reaction mixture was poured into a large amount of saturated saline solution
  2. extractionextracted with chloroform
  3. washAfter washing with water the extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. distillationChloroform was distilled off
  6. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-5aa015a78dbd494981f98f4ca868353f
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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