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Chemical Structure| 10314-99-5 Chemical Structure| 10314-99-5

Structure of 10314-99-5

Chemical Structure| 10314-99-5

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Product Details of [ 10314-99-5 ]

CAS No. :10314-99-5
Formula : C14H16ClNO3
M.W : 281.73
SMILES Code : ClC(=O)C1CCN(CC1)C(=O)OCC1=CC=CC=C1
MDL No. :MFCD02677707
InChI Key :KUBUQFFBRSHOMJ-UHFFFAOYSA-N
Pubchem ID :2776270

Safety of [ 10314-99-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 10314-99-5 ]

* 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 [ 10314-99-5 ]

[ 10314-99-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1885-32-1 ]
  • [ 10314-99-5 ]
  • [ 476493-02-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h; 2-Amino-3-methylbenzamide (6.0 g) and triethylamine (11.2 ml) were dissolved in dimethylformamide (60 ml), and 1-(benzyloxycarbonyl)piperidin-4-ylcarbonyl chloride (16.9 g) was added to the mixture under ice-cooling. The mixture was stirred at room temperature for 2 hr, and water and chloroform were added. The precipitated crystals were collected by filtration to give 2-((1-(benzyloxycarbonyl)piperidin-4-yl)carbonyl)amino-3-methylbenzamide (6.8 g). The filtrate was extracted with chloroform and dried over magnesium sulfate. The solvent was concentrated, and the precipitated crystals were collected by filtration with chloroform to give 2.2 g of the compound. The filtrate was concentrated and purified by silica gel column chromatography to give 2.0 g of the compound. A total of 11 g was obtained. This compound was suspended in a mixed solvent of pyridine (28 ml) and water (28 ml), and 2N aqueous sodium hydroxide (2.8 ml) was added. The mixture was stirred at room temperature for 4 days. After the completion of the reaction, the precipitated crystals were collected by filtration and washed with water to give 2-(1-(benzyloxycarbonyl)piperidin-4-yl)-8-methyl-3H-quinazolin-4-one (8.7 g). This compound (8.7 g) was dissolved in a solution of hydrobromic acid in acetic acid, and the mixture was stirred overnight. After the completion of the reaction, the precipitated crystals were collected by filtration to give hydrobromide. The crystals were alkalized and recrystallized from ethanol to give 8-methyl-2-(piperidin-4-yl)-3H-quinazolin-4-one (5 g). 1H-NMR(400MHz,DMSO-d6) d: 1.62-1.83(4H,m), 2.42-2.56(4H,m), 2.51(3H,S), 2.60-2.68(1H,m), 2.95-3.05(2H,m), 3.32(1H,brS), 7.31(1H,t,J=8Hz), 7.62(1H,d,J=8Hz), 7.90(1H,d,J=8Hz).
  • 2
  • [ 17672-21-8 ]
  • [ 10314-99-5 ]
  • [ 1175529-79-9 ]
YieldReaction ConditionsOperation in experiment
20% With triethylamine; In dichloromethane; at 0 - 20℃; Example 151 A & B; A: benzyl-4-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)piperidine-1-carboxylateB: 1-benzyl 4-(2-(1-(benzyloxycarbonyl)piperidine-4-carboxamido)-6-(methoxycarbonyl)phenyl)piperidine-1,4-dicarboxylateTo the solution of piperidine-4-carboxylic acid (1.3 g, 10 mmol) of water (20 ml) was added sodium hydroxide (1.6 g, 40 mmol). Then benzyloxycarbonyl chloride (2.02 g, 12 mmol) was added dropwise at 0 C. The mixture was stirred at 0 C. for 2 h. The resulting mixture was treated with 5N hydrochloric acid to pH=6 and extracted with ethyl acetate, the solvent was removed under reduced pressure and dried in vacuum. 2.2 g of crude 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid was obtained. To a stirred solution of crude 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid (1.05 g, 4 mmol) in anhydrous dichloromethane (10 mL) was added dropwise thionyl chloride (0.573 g, 4.81 mmol) at 0 C. After the addition, the solution was stirred at room temperature overnight. Solvent was removed in vacuum to give crude benzyl-4-(chlorocarbonyl)piperidine-1-carboxylate. To a stirred solution of ethyl 3-amino-2-hydroxybenzoate (0.501 g, 3.0 mmol) and triethylamine (0.455 g, 4.5 mmol) in anhydrous dichloromethane (20 mL) was added dropwise a solution of crude benzyl-4-(chlorocarbonyl)piperidine-1-carboxylate (1.014 g, 3.6 mmol) in anhydrous dichloromethane (5 mL) at 0 C. After the addition, the mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane, washed with water (30 mL×3), brine (30 mL), dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=30:1 to 5:1) to give benzyl-4-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)piperidine-1-carboxylate (0.25 g, yield 20%; LC-MS (ESI) m/z: 413 (M+1)+) and 1-benzyl 4-(2-(1-(benzyloxyarbonyl)piperidine-4-carboxamido)-6-(methoxyarbonyl)phenyl)piperidine-1,4-dicarboxylate (1.0 g, yield 51%; LC-MS (ESI) m/z: 658 (M+1)+).
 

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