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Chemical Structure| 182919-58-0 Chemical Structure| 182919-58-0

Structure of 182919-58-0

Chemical Structure| 182919-58-0

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Product Details of [ 182919-58-0 ]

CAS No. :182919-58-0
Formula : C13H19N3O
M.W : 233.31
SMILES Code : O=C(C1CN(CC2=CC=CC=C2)CCC1)NN
MDL No. :MFCD00978691

Safety of [ 182919-58-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 182919-58-0 ]

* 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 [ 182919-58-0 ]

[ 182919-58-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 72551-53-2 ]
  • [ 182919-58-0 ]
YieldReaction ConditionsOperation in experiment
99% With hydrazine hydrate; In ethanol;Reflux; A mixture of <strong>[72551-53-2]ethyl 1-benzylpiperidine-3-carboxylate</strong> (9) (5.1 g,20.62 mmol, 1 eq.) and hydrazine monohydrate (10 mL, 10 eq.) inethanol (10 mL) was stirred overnight under reflux. After cooling,the solvent and excess of hydrazine were removed under reducedpressure to afford compound 10 as colorless oil in yield of 99%; 1HNMR (400 MHz, CDCl3) delta 9.00 (s br, 1H, NH), 7.32e7.17 (m, 5H, Ar-H), 3.79 (s br, 2H, NH2), 3.47 (d, J 12.4 Hz, 1H, CHa-Ph), 3.38 (d,J 12.4 Hz, 1H, CHb-Ph), 2.62 (m, 2H, piperidin-H), 2.45 (m, 1H,piperidin-H), 2.23 (m, 2H, piperidin-H), 1.87 (m, 1H, piperidin-H),1.72-1.48 (m, 3H, piperidin-H); 13C NMR (100 MHz, CDCl3)delta 175.4, 137.3, 129.2, 128.4, 127.4, 63.4, 54.4, 53.7, 40.8, 26.7, 22.7;HRESI-MS m/z calcd. for [M+H]+ C13H20N3O: 234.1601, found:234.1604.
92% With acetic acid; hydrazine; In ethanol; for 72h;Heating / reflux; Acetic acid (20 mL) and hydrazine hydrate (136 mL (140 g, 2.8 mol) were added to a solution of (3RS)- ethyl l-(phenylmethyl)-3-piperidinecarboxylate (Description 72, 270 g, 1.092 mol) in ethanol (310 mL) and the mixture was heated under reflux for 3 days. The mixture was cooled and the solvent was partly evaporated under reduced pressure until a precipitation occurred. The solid was collected, aqueous KOH (50 g in 100 mL) was added and the mixture was extracted with CHCl3 (2 x 300 mL). The combined organic fractions were dried (Na2SO4) the solvent was partly evaporated under reduced pressure until a precipitation occurred. The solid was collected, the filtrate was diluted with Et2O (200 mL) and further solid was collected. The combined solids were washed with Et2O and dried in vacuo to give the title compound as a solid (217 g, 92%).
With hydrazine hydrate; In ethanol;Reflux; General procedure: Each ethyl N-substituted nipecotate derivative/ethyl N-substitutedisonipecotate derivative (1 mol) in 30 mL ethanol and hydraziniumhydroxide (10 mol) were heated under microwave irradiation (130 C,300 W) or refluxed for 24-48 h in an oil bath. After completion of thereaction (TLC), ethanol was evaporated and the residue was extractedwith dichloromethane or diethyl ether. The solvent was evaporatedunder reduced pressure until an oily residue occured. Then n-hexanewas added to the residue to give the title compound as a white solid.The precipitated crystals were separated by filtration.
 

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