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Chemical Structure| 160357-88-0 Chemical Structure| 160357-88-0

Structure of 160357-88-0

Chemical Structure| 160357-88-0

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CAS No.: 160357-88-0

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Product Details of [ 160357-88-0 ]

CAS No. :160357-88-0
Formula : C11H17N3
M.W : 191.27
SMILES Code : NC1CCN(CC2=CC=CN=C2)CC1
MDL No. :MFCD08059920
InChI Key :MSXJQLZTWITCEC-UHFFFAOYSA-N
Pubchem ID :6484204

Safety of [ 160357-88-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 160357-88-0 ]

* 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 [ 160357-88-0 ]

[ 160357-88-0 ] Synthesis Path-Downstream   1~4

YieldReaction ConditionsOperation in experiment
Method 1 Scheme B, step a: 4-Carboxamide-1-(3-pyridinylmethyl)piperidine 4-Carboxamide-1-(3-pyridinylmethyl)piperidine may be prepared from isonipecotamide and 3-picolyl chloride hydrochloride essentially as described above in Example 38, Scheme B, step a. Scheme B, step b: 4-Amino-1-(3-pyridinylmethyl)piperidine 4-Amino-1-(3-pyridinylmethyl)piperidine is prepared from 4-carboxamide-1-(3-pyridinylmethyl)piperidine essentially as described above in Example 38, Scheme B, step b.
c. 38.05 Grams of N-(3-pyridylmethyl)-4-piperidone and 27.8 grams of hydroxylammonium hydrochloride were dissolved in 600 milliliters of ethanol. 300 milliliters of 30% sodium hydroxide were added and the solution refluxed for half an hour, and then 40 grams of nickel, aluminium alloy were carefully added portionwise to the refluxing solution. The solution was refluxed for a further 3 hours, cooled and filtered through kieselguhr. The solution was evaporated and the residue treated with ether. The combined ether extracts were dried over magnesium sulphate and evaporated to give 33.72 grams of 4-amino-N-(3-pyridylmethyl)piperidine.
With hydrogenchloride; In 1,4-dioxane; water; at 20.0℃; for 2.0h; General procedure: The product from the previous step was dissolved in dioxane (15 mL). Cone. HC1 (2 mL, 25 mmol) was added and the reaction mixture was stirred at RT for 2 h. The mixture was evaporated to a small volume and water (8 mL) was added. The resulting aqueous phase was washed with EtOAc (15 mL). The pH of the aqueous phase was adjusted with 8M NaOH to approximately pH12, and then extracted with EtOAc (3x25 mL). The combined organic phases were washed with brine (5 mL), dried over Na2S04 and finally evaporated to yield 940 mg (92% over two steps) of pure title product as clear almost colorless oil. 1H NMR (600 MHz, CD3OD) δ ppm 7.19 (t, J=7.6 Hz, 1 H) 7.14 (s, 1 H) 7.09 (t, J=8.2 Hz, 2 H) 3.46 (s, 2 H) 2.85 (d, J=12.2 Hz, 2 H) 2.56 - 2.65 (m, 1 H) 2.33 (s, 3 H) 2.05 (td, J=l 1.9, 2.1 Hz, 2 H) 1.79 (d, J=13.4 Hz, 2 H) 1.40 (qd, J=12.0, 3.8 Hz, 2 H). MS (ESI+) m/z 205 [M+H]+.
  • 2
  • [ 431897-72-2 ]
  • [ 160357-88-0 ]
YieldReaction ConditionsOperation in experiment
11.2 g (88%) With sodium borohydrid; In 1,4-dioxane; ethanol; water; Step b 1-(3-pyridylmethyl)-4-aminopiperidine 20.8 g (0.53 mol) of sodium borohydride are added to a solution of 19 9 (0.066 mol) of 2,2,2-trifluoro-N-[1-(3-pyridylmethyl)4-piperidyl]acetamide in 640 ml of dioxane and 64 ml of absolute ethanol, and the resulting mixture is refluxed under nitrogen for 10.5 hours. After concentrating and taking up the residue in water, the mixture is extracted with dichloromethane. The organic phase is dried over sodium sulphate and concentrated to give 11.2 g (88%) of an oil, which is used without further purification in the following step.
  • 3
  • [ 160357-88-0 ]
  • [ 1257847-84-9 ]
  • [ 1257847-91-8 ]
  • 4
  • [ 160357-88-0 ]
  • [ 624-65-7 ]
  • C14H19N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With sodium hydrogencarbonate; In ethanol; at 78.0℃; for 3.0h; General procedure: To a solution of compound 4a-f (12.53 mmol) andNaHCO3 (2.63 g, 31.31 mmol) in ethanol (10 ml) was addedcompound 3 (0.98 g, 13.15 mmol) in ethanol (6 ml) solutionat 78 C for about 3 h. The reaction mixture was filteredthrough a celite pad to remove NaHCO3. The solvent wasevaporated under vacuum. The crude material was purifiedby column chromatography to obtain product.
 

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