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Chemical Structure| 128200-13-5 Chemical Structure| 128200-13-5

Structure of 128200-13-5

Chemical Structure| 128200-13-5

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Product Details of [ 128200-13-5 ]

CAS No. :128200-13-5
Formula : C8H16N2O
M.W : 156.23
SMILES Code : OC1(CN)CN2CCC1CC2
English Name :3-(Aminomethyl)quinuclidin-3-ol
MDL No. :MFCD12407453

Safety of [ 128200-13-5 ]

Application In Synthesis of [ 128200-13-5 ]

* 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 [ 128200-13-5 ]

[ 128200-13-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 6238-30-8 ]
  • [ 128200-13-5 ]
YieldReaction ConditionsOperation in experiment
With borane In tetrahydrofuran for 12h; Heating;
Multi-step reaction with 2 steps 1: 80 percent / borane / tetrahydrofuran / 12 h / Heating 2: HCl
  • 2
  • [ 61694-98-2 ]
  • [ 128200-13-5 ]
  • [ 530-62-1 ]
  • [ 144150-39-0 ]
YieldReaction ConditionsOperation in experiment
2.67 g (54%) In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile 1 5-Chloro-N-(3-hydroxy-1-azabicyclo[2.2.2]oct-3-ylmethyl)-2-methoxy-4-(methylamino)benzamide EXAMPLE 1 5-Chloro-N-(3-hydroxy-1-azabicyclo[2.2.2]oct-3-ylmethyl)-2-methoxy-4-(methylamino)benzamide A solution of 5-chloro-2-methoxy-4-(methylamino)benzoic acid (3.02 g, 0.014 mole) in anhydrous tetrahydrofuran (15 ml) under nitrogen was treated with 1,1'-carbonyldiimidazole (2.35 g, 0.0145 mole) and stirred for one hour. A solution/suspension of 3-aminomethyl-1-azabicyclo[2.2.2]octan-3-ol (2.34 g, 15 mole) in tetrahydrofuran (15 ml) containing a little N,N-dimethylformamide for solubility was added slowly over a few minutes, and the mixture was stirred overnight (18 hours) at room temperature and for one hour at 60° C., then concentrated in vacuo. The white solid was partitioned between 1.0N sodium carbonate (100 ml) and methylene chloride (200 ml) containing a little methanol, and the organic layer was separated. The aqueous solution was extracted with methylene chloride (2*50 ml) containing a little methanol, and the combined organic solution was dried (sodium sulfate) and passed through a short column of alumina (eluted with 10% methanol/methylene chloride). The filtrate was concentrated in vacuo, triturated from ether, and triturated from acetonitrile to afford 2.67 g (54%) of the title compound as a colorless solid; mp 236°-237° C. (dec). Analysis: Calculated for C17 H24 ClN3 O3: C, 57.70; H, 6.84; N, 11.88. Found: C, 57.45; H, 6.88; N, 11.86.
  • 3
  • [ CAS Unavailable ]
  • [ 128200-13-5 ]
  • [ 138272-95-4 ]
  • [ 617-36-7 ]
YieldReaction ConditionsOperation in experiment
With Hg In dichloromethane 1.i (i) (i) Ethyl acetamidate method 3-Aminomethylquinuclidin-3-ol (9.1 g., 0.058 mole) was dissolved in 500 ml. dichloromethane; ethyl acetamidate-HCl salt (14 g., 0.11 mole) was added and the mixture was stirred at 5° C. for six hours. The solution was made alkaline with Dowex 1, filtered and the solvent was evaporated to yield an oily residue, which was distilled at 60°-65° C./0.5 mm. Hg to yield AF125 as a colorless liquid. MS (M+)181 base peak, 139 (M-CH3 CN). 1 H-NMR (CDCl3 -TMS): δ 1.97(dd,3H)(J=1.3 Hz); 2.8-2.9(m,1H); 3.14(d,1H)(J=12 Hz); 3.5(dd,1H)(J=13 Hz), 1.3 Hz); 3.96(dd,1H)(J=13 Hz, 1.3 Hz). 1 H-NMR including spin decoupling experiments enable the assignment of the hydrogens adjacent to C2, C9 and the methyl group. Each of the hydrogens adjacent to C9 shows a double doublet (J=13 Hz geminal coupling) and a homo-allylic coupling with the methyl group (J=1.3 Hz). Irradiation at 1.97 (methyl group) brings about the disappearance of the homo-allylic coupling at 3.5 and 3.9 ppm and vice versa. Irradiation at 3.5 effects the signal at 3.96 and vice versa which must be due to geminal coupling of H9a and H9b (Table 1). The 13 C-NMR spectrum (in CDCl3) is very informative and enables the assignment of most resonances to the appropriate carbons. 13 C-NMR (CDCl3 -TMS): δ 13.2(CH3); 20.5 (CH2 CH); 21.5(CH2 CH); 30.0 (CHCH2); 45.3, 45.7(CH2 CH2 N); 62.2, 64.2(CH2 N); 84.0(COCH2); 165(CCH3).
 

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