ChemicalBook CAS DataBase List 1-(3-Nitrophenyl)piperidine

1-(3-Nitrophenyl)piperidine synthesis

8synthesis methods

Product Name:1-(3-Nitrophenyl)piperidine
CAS Number:27969-73-9
Molecular formula:C11H14N2O2
Molecular Weight:206.24

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402-67-5 Synthesis

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Yield:27969-73-9 742 mg

Reaction Conditions:

in N,N-dimethyl-formamide at 100;

Steps:

4-(4-Nitrophenyl)morpholine (S2)

1-Chloro-4-nitrobenzene (500 mg, 3.17 mmol) and K₂CO₃ (526 mg, 3.8 mmol, 1.2 equiv.) were added together with DMF (10 mL) and stirred at RT. Morpholine (440 μL, 5.1 mmol, 1.6 equiv.) was added to the reaction mixture which was heated at 100 °C overnight. After cooling down to RT, the mixture was extracted with EA. The EA layer was washed with DI-water three times and the combined water layers were back-extracted with EA three times. The combined EA extracts were dried (Na₂SO₄) and all solvent was evaporated under vacuum. The residue was purified by flash chromatography (elution system - EA : Hexane = 1 : 1 ) to give the title compound as a yellow solid (294 mg, 1.41 mmol). R_f = 0.35 (EA/Hexane = 1 : 1); ¹H NMR (400 MHz, CDCl₃) δ 8.15 (d, J = 9.4 Hz, 2H), 6.84 (d, J = 9.4 Hz, 2H), 3.92 - 3.82 (m, 4H), 3.41 - 3.34 (m, 4H).

References:

Chu-Farseeva, Yu-yi;Mustafa, Nurulhuda;Poulsen, Anders;Tan, Eng Chong;Yen, Jeffrey J.Y.;Chng, Wee Joo;Dymock, Brian W. [European Journal of Medicinal Chemistry,2018,vol. 158,p. 593 - 619] Location in patent:supporting information

110-89-4
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$15.96/100ML