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Chemical Structure| 26905-03-3 Chemical Structure| 26905-03-3

Structure of 4-(4-Nitrophenyl)piperidine
CAS No.: 26905-03-3

Chemical Structure| 26905-03-3

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Product Details of [ 26905-03-3 ]

CAS No. :26905-03-3
Formula : C11H14N2O2
M.W : 206.24
SMILES Code : O=[N+](C1=CC=C(C2CCNCC2)C=C1)[O-]
MDL No. :MFCD06804549
Boiling Point : No data available
InChI Key :CDSJZBOLNDWPAA-UHFFFAOYSA-N
Pubchem ID :15925817

Safety of [ 26905-03-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of [ 26905-03-3 ]

* 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 [ 26905-03-3 ]

[ 26905-03-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 401564-36-1 ]
  • [ 26905-03-3 ]
  • [ 401568-12-5 ]
  • 2
  • [ 10272-49-8 ]
  • [ 26905-03-3 ]
YieldReaction ConditionsOperation in experiment
68% 4-Phenyl-1,2,3,6-tetrahydropyridine hydrochloride (10.38 g; 53.0 mmol) dissolved in methanol (160 ml) in the presence of palladium-on-charcoal (5%) (1.04 g) is hydrogenated under 30 psi of hydrogen for 1 hour.The medium is filtered through Celite and the filtrate is evaporated to dryness to give <strong>[10272-49-8]4-phenylpiperidine hydrochloride</strong> (10.17 g; 97%).This intermediate (13 g; 65.7 mmol) is taken up in chloroform (430 ml), cooled to 0 C. and then treated with copper nitrate 2.5-hydrate (15.3 g; 65.7 mmol) for 15 minutes.The mixture is then added dropwise over 45 minutes to a solution of trifluoroacetic anhydride (65 ml; 460 mmol) in chloroform (70 ml).After stirring at 0 C. for 48 hours, the medium is poured onto ice, diluted with dichloromethane and neutralized by addition of concentrated sodium hydroxide (85 ml).The medium is extracted several times with dichloromethane and the organic phases are then combined, dried over magnesium sulfate, filtered and evaporated to dryness.The syrup obtained is purified by chromatography on a column of silica eluted with a 96.5/3/0.5 CH2Cl2/MeOH/NH4OH mixture to give pure compound 141A (8.35 g; 68%). 1H NMR, d6-DMSO (ppm): 1.52 m, 2H; 2.59 t, 2H; 2.75 dt, 1H; 3.19 broad s, 2H; 7.52 d, 2H; 8.16 d, 2H;
4-Phenylpiperidine hydrochloride (3 g, 15 mmol) was dissolved in concentrated sulfuric acid (3 g), followed by dropwise addition of concentrated nitric acid at 0C. The solution was slowly warmed to rt and left at this temperature for 1 day. The mixture was poured into ice water and treated with 1N NAOH until basic. The solution was then extracted by ethyl ether. The extracts were combined, dried over MGS04, and evaporated. The residue was recrystalized in ethyl ether to provide pure product (1.5 g). LC-MS M+H 207.
 

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