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Chemical Structure| 25225-13-2 Chemical Structure| 25225-13-2

Structure of 25225-13-2

Chemical Structure| 25225-13-2

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Product Details of [ 25225-13-2 ]

CAS No. :25225-13-2
Formula : C12H21NO
M.W : 195.30
SMILES Code : NCCOC12CC3CC(C2)CC(C3)C1
MDL No. :MFCD02632387

Safety of [ 25225-13-2 ]

Application In Synthesis of [ 25225-13-2 ]

* 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 [ 25225-13-2 ]

[ 25225-13-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1480-65-5 ]
  • [ 25225-13-2 ]
  • N-[2-(1-adamantyloxy)ethyl]-5-chloropyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 24h;Inert atmosphere; General procedure: An argon filled one-neck flask equipped with a magnetic stir bar and reflux condenser was charged with 2-fluoropyridine 1a (146 mg, 1.5 mmol), finely powdered potassium carbonate (276 mg, 2 mmol), DMF (1 mL), and the corresponding amine (0.5 mmol). The reaction mixture was stirred at 140 °C for 24 h. In the case of diamine 2p (0.5 mmol), 291 mg (3 mmol) of compound 1a and 552 mg (4 mmol) of K2CO3 were used. 2-Fluoro-5-halopyridines 1b-d were used in the amount of 0.5 mmol. After completion of the reaction, the mixture was diluted with dichloromethane (5 mL), the precipitate was filtered off and washed with dichloromethane (5 mL). The organic layers were combined and concentrated in vacuo. The obtained residues were analyzed by NMR spectroscopy. If required, the products were isolated by column chromatography using gradient elution as follows: petroleum ether-CH2Cl2 (4 : 1 1 : 4),CH2Cl2, CH2Cl2-MeOH (500 : 1 3 : 1). Spectral data for compounds 3d,e,q have been published in work,18 for compounds 3a-c,g,i,m,n, in work.23
  • 2
  • [ 7089-68-1 ]
  • [ 25225-13-2 ]
  • C24H27N3O [ No CAS ]
  • 3
  • [ 66127-01-3 ]
  • [ 25225-13-2 ]
  • C24H27N3O [ No CAS ]
  • 4
  • [ 40000-20-2 ]
  • [ 25225-13-2 ]
  • C24H27N3O [ No CAS ]
  • 5
  • [ 25225-13-2 ]
  • [ 175205-81-9 ]
  • N-[2-(adamantan-1-yloxy)ethyl]-4-(trifluoromethyl)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With copper(l) iodide; 2-(2-methyl-1-oxopropyl)cyclohexanone; caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 24h;Schlenk technique; General procedure: a. Palladium(0)-catalyzed reactions. A Schlenk flask was charged with Pd(dba)2 (1-8 mol %, 2.9-23 mg), phosphine ligand (1.25-9 mol %), and bromopyridine2-8 (0.5 mmol), and 5 mL of dioxane, amine 1 or 21 (0.625 mmol), and sodium tert-butoxide(0.75 mmol, 72 mg) were added. The mixture was refluxed for 12 h with stirring and cooled to room temperature, the organic phase was separated, the precipitate was washed with methylene chloride (5 mL),and the organic phase was combined with the washings and evaporated under reduced pressure. The residue was dissolved in methylene chloride (5 mL), and the solution was washed with water (3 × 5 mL), dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). b. A Schlenk flask was charged with copper(I)iodide (10 or 20 mol %, 9.5 or 19 mg), 2-isobutyrylcyclohexanone(20 or 40 mol %, 17 or 34 mg), and bromopyridine 2-8 (0.5 mmol), and 1 mL of DMF,amine 1 or 21 (0.5 mmol), and cesium carbonate(0.75 mmol, 250 mg) were added. The mixture was heated for 24 h at 140C with stirring and cooled to room temperature, the organic phase was separated,and the residue was washed with methylene chloride(5 mL). The organic phase was combined with the washings and evaporated under reduced pressure, the residue was dissolved in methylene chloride (5 mL),and the solution was washed with water (3 × 5 mL),dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). The spectral parameters of compounds 9, 16 [21], 22, and 29 [26]were consistent with published data
  • 6
  • [ 25225-13-2 ]
  • [ 175205-81-9 ]
  • N-[2-(adamantan-1-yloxy)ethyl]-4-(trifluoromethyl)pyridin-2-amine [ No CAS ]
  • N-[2-(adamantan-1-yloxy)ethyl]-4-(trifluoromethyl)-N-[4-(trifluoromethyl)pyridin-2-yl]pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74%; 14% With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; for 12h;Reflux; Schlenk technique; General procedure: a. Palladium(0)-catalyzed reactions. A Schlenk flask was charged with Pd(dba)2 (1-8 mol %, 2.9-23 mg), phosphine ligand (1.25-9 mol %), and bromopyridine2-8 (0.5 mmol), and 5 mL of dioxane, amine 1 or 21 (0.625 mmol), and sodium tert-butoxide(0.75 mmol, 72 mg) were added. The mixture was refluxed for 12 h with stirring and cooled to room temperature, the organic phase was separated, the precipitate was washed with methylene chloride (5 mL),and the organic phase was combined with the washings and evaporated under reduced pressure. The residue was dissolved in methylene chloride (5 mL), and the solution was washed with water (3 × 5 mL), dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). b. A Schlenk flask was charged with copper(I)iodide (10 or 20 mol %, 9.5 or 19 mg), 2-isobutyrylcyclohexanone(20 or 40 mol %, 17 or 34 mg), and bromopyridine 2-8 (0.5 mmol), and 1 mL of DMF,amine 1 or 21 (0.5 mmol), and cesium carbonate(0.75 mmol, 250 mg) were added. The mixture was heated for 24 h at 140C with stirring and cooled to room temperature, the organic phase was separated,and the residue was washed with methylene chloride(5 mL). The organic phase was combined with the washings and evaporated under reduced pressure, the residue was dissolved in methylene chloride (5 mL),and the solution was washed with water (3 × 5 mL),dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). The spectral parameters of compounds 9, 16 [21], 22, and 29 [26]were consistent with published data
19%; 38% With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In 1,4-dioxane; at 100℃; for 12h;Schlenk technique; General procedure: a. Palladium(0)-catalyzed reactions. A Schlenk flask was charged with Pd(dba)2 (1-8 mol %, 2.9-23 mg), phosphine ligand (1.25-9 mol %), and bromopyridine2-8 (0.5 mmol), and 5 mL of dioxane, amine 1 or 21 (0.625 mmol), and sodium tert-butoxide(0.75 mmol, 72 mg) were added. The mixture was refluxed for 12 h with stirring and cooled to room temperature, the organic phase was separated, the precipitate was washed with methylene chloride (5 mL),and the organic phase was combined with the washings and evaporated under reduced pressure. The residue was dissolved in methylene chloride (5 mL), and the solution was washed with water (3 × 5 mL), dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). b. A Schlenk flask was charged with copper(I)iodide (10 or 20 mol %, 9.5 or 19 mg), 2-isobutyrylcyclohexanone(20 or 40 mol %, 17 or 34 mg), and bromopyridine 2-8 (0.5 mmol), and 1 mL of DMF,amine 1 or 21 (0.5 mmol), and cesium carbonate(0.75 mmol, 250 mg) were added. The mixture was heated for 24 h at 140C with stirring and cooled to room temperature, the organic phase was separated,and the residue was washed with methylene chloride(5 mL). The organic phase was combined with the washings and evaporated under reduced pressure, the residue was dissolved in methylene chloride (5 mL),and the solution was washed with water (3 × 5 mL),dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). The spectral parameters of compounds 9, 16 [21], 22, and 29 [26]were consistent with published data
 

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