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Chemical Structure| 538-09-0 Chemical Structure| 538-09-0
Chemical Structure| 538-09-0

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Synonyms: Nortropenol

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Product Details of Nortropine

CAS No. :538-09-0
Formula : C7H13NO
M.W : 127.18
SMILES Code : O[C@H]1C[C@H](N2)CC[C@H]2C1
Synonyms :
Nortropenol
MDL No. :MFCD00047140

Safety of Nortropine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of Nortropine

* 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 [ 538-09-0 ]

[ 538-09-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 67515-59-7 ]
  • [ 538-09-0 ]
  • 4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)-3-trifluoromethylbenzo-nitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With pyridine; at 110℃; for 20h; Example 25 4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)-3-trifluoromethylbenzo-nitrile (196MBT10-B) Nortropine (269 mg, 2.12 mmol) and <strong>[67515-59-7]4-fluoro-3-(trifluoromethyl)benzonitrile</strong> (100 mg, 0.529 mmol) were dissolved in pyridine (2 mL). The mixture was heated to 110 C. in a sealed flask for 20 hours and then concentrated. The residue was dissolved in 2 M HCl (20 mL) and extracted with dichloromethane (2×20 mL). The combined organic phases were dried over Na2SO4, filtered and evaporated, and the resulting oil was purified by preparative TLC (eluting with dichloromethane) to afford 55 mg (35%) of the title compound as a colorless solid. LCMS m/z 297 [M+H]+. 1H-NMR (CDCl3) delta 7.80-6.85 (m, 3H), 4.15-4.00 (m, 3H), 2.33-2.10 (m, 4H), 2.00-1.84 (m, 2H), 1.82-1.70 (m, 2H), 1.39 (s, 1H).
  • 2
  • [ 796600-15-2 ]
  • [ 538-09-0 ]
  • 2-chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-3-methylbenzonitrile, hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% Example 4 2-Chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-3-methylbenzonitrile, hydrochloride (165RL90) <strong>[796600-15-2]2-Chloro-4-fluoro-3-methylbenzonitrile</strong> (165RL87a, 55 mg, 0.32 mmol) and nortropine (165 mg, 1.29 mmol) was dissolved in pyridine (2 mL) and the mixture irradiated at 220 C. for 2 hours in a microwave oven. Dichloromethane (50 mL) was added and the mixture washed with hydrochloric acid (0.4 M, 2×30 mL) followed by sat. sodium hydrogen carbonate (20 mL). The organic layer was dried over sodium sulfate, filtered and evaporated. The product was further purified by column chromatography using dichloromethane to give the title compound (16.2 mg, 18%). Rf=0.45 (CH2Cl2). LC/MS m/z 277 [M+H]+. 1H-NMR (CDCl3, 300 MHz) delta 7.37 (d, 1H, J=8.6, Ar-H), 6.78 (d, 1H, J=8.6, Ar-H), 4.20 (m, 1H, Tr-H), 3.80 (m, 2H, Tr-H), 2.37 (s, 3H, Ar-CH3), 2.32-2.22 (m, 4H, Tr-H), 1.98-1,81 (m, 4H, Tr-H).
  • 3
  • [ 796600-15-2 ]
  • [ 538-09-0 ]
  • 2-chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-3-methylbenzonitrile [ No CAS ]
 

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