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Chemical Structure| 25163-62-6 Chemical Structure| 25163-62-6

Structure of 25163-62-6

Chemical Structure| 25163-62-6

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Product Details of [ 25163-62-6 ]

CAS No. :25163-62-6
Formula : C16H24N2O4
M.W : 308.37
SMILES Code : OC1=C(CN2CCOCC2)C=CC(CN3CCOCC3)=C1O
MDL No. :MFCD01412258

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Application In Synthesis of [ 25163-62-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 25163-62-6 ]

[ 25163-62-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 25163-62-6 ]
  • [ 2785-78-6 ]
YieldReaction ConditionsOperation in experiment
With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 70℃; under 37494.2 Torr; for 48.0h; A mixture of 4 (12.3 g, 40 mmol) and 10% Pd/C (3.7 g) in dry THF (60 mL) was hydrogenated at 70 C under 725 psi of hydrogen gas for 48 h. The crude mixture was filtered through Celite, and the solvent was evaporated to afford dimethyl catechol 5, which was subjected to the next step without purification. Aluminum (III) chloride (21.3 g, 160 mmol) was slowly added to a solution of crude 5 and triethyl orthoformate (13.3 mL, 80 mmol) in dry toluene (150 mL), and the mixture was stirred at 60C for 2 h until TLC indicated complete conversion of the starting material. Hydrochloric acid (3 N, 17 mL) was added, and the reaction mixture was further stirred at rt for 1 h. Ethyl acetate (500 mL) was then added, the reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. The resulting residue was dissolved in ethyl acetate (500 mL), washed with brine (500 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure. Since NMR and MS analyses of the residue showed the formation of 6, the crude material was subjected to the next reaction without purification. Benzyl bromide (23.2 mL, 196.1 mmol) was added dropwise to a solution of crude 6, potassium carbonate (37.8 g, 273.5 mmol) and potassium iodide (3.0 g, 18.1 mmol) in dry acetone (100 mL), and the mixture was refluxed for 13h. The solution was diluted with ethyl acetate (400 mL), washed with brine (3 x300 mL), and dried over sodium sulfate. After removal of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel (3:1 n-hexane - ethyl acetate) to give 444 mg (total yield from 4: 3.2%) of compound 7.
 

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