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Chemical Structure| 923035-05-6 Chemical Structure| 923035-05-6

Structure of 923035-05-6

Chemical Structure| 923035-05-6

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Product Details of [ 923035-05-6 ]

CAS No. :923035-05-6
Formula : C13H20N2O2
M.W : 236.31
SMILES Code : O=C(OC1=CC=CC([C@@H](NC)C)=C1)N(CC)C

Safety of [ 923035-05-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H300-H411
Precautionary Statements:P264-P270-P273-P301+P310+P330-P391-P405-P501
Class:6.1
UN#:2810
Packing Group:

Application In Synthesis of [ 923035-05-6 ]

* 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 [ 923035-05-6 ]

[ 923035-05-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 50-00-0 ]
  • [ 923035-05-6 ]
  • [ 141-53-7 ]
  • [ 123441-03-2 ]
YieldReaction ConditionsOperation in experiment
Example 8; Obtaining (S)-N-ethyl-3-[1-(dimethylamino)ethyl]-N-methylphenylcarbamate [Rivastigmine] 2.5 mL of 98% formic acid, 0.4 g of sodium formiate and 1 mL of 37% formaldehyde aqueous solution are added to 0.5 g of the compound of formula (II) [Example 7]. The mixture is heated under reflux and maintained at this temperature until the end of the reaction. It is processed by adding 5 mL of methylene chloride and the mixture is adjusted to pH 8.7. The separated organic phase is distilled until obtaining a residue that is purified by column chromatography and is identified as the desired product. 1H NMR: delta 1.15-1.2 (2*t, 3H, N-CH2-CH3) ; delta 1.3 (d, 3H, -CH-CH3) ; delta 2.2 (s, 6H, N-CH3); delta 2.96-3.04 (2*s, 3H, OCN-CH3); 3.2 (q, 1H, -CH-CH3) ; delta 3.36-3. 44 (2*q, 2H, N-CH2-CH3) ; delta 6.96 (d, 1H, Ar-H); delta 7.05 (s, 1H, Ar-H); delta 7.10 (d, 1H, Ar-H); delta 7.3 (t, 1H, Ar-H)
  • 2
  • [ 50-00-0 ]
  • [ 923035-05-6 ]
  • [ 123441-03-2 ]
YieldReaction ConditionsOperation in experiment
79.3% Example 9: Preparation of N-methylethylcarbamino-3-[(S)-1-(dimethylamino) ethyl] phenyl ester (the compound represented by formula (VII)); 11.27g (39.2mmol) the compound represented by formula (VI) obtained in Example 4 and 7.22g (157mmol) formic acid were mixed at room temperature, and then 6.54g (78.4mmol) formaldehyde aqueous solution (37mass%) was added. The mixture was fluxed for 2 hours, and then cooled to room temperature. 50ml water was added, followed by adding sodium carbonate in batches to adjust pH to 8. The result was then extracted with 60ml ethyl acetate twice. The combined organic layers was washed with 15ml water, and then dried with anhydrous magnesium sulfate. Colorless liquid (11.3g) was obtained after filtering and recovering the solvent under a reduced pressure. Vacuum distillation: 1 to 1.5 kpa, the fraction at a temperature ranging from 128C to 133C is collected, and 7.77g product is obtained with a yield of 79.3%. Optical rotation [alpha]20D = -32.1, C=5, ethanol. 1H NMR (CDCl3) delta ppm: 1.22 (m, 3H), 1.35 (q, 3H), 2.20 (s, 6H), 3.02 (d, 3H), 3.25 (m, 1H), 3.44 (s, 2H), 7.05 (m, 3H), 7.27 (m, 1H); MS (ESI) m/z: 251.2(M++1).
Example 5; Obtaining (S)-N-ethyl-3-[1-(dimethylamino)ethyl]-N-methylphenylcarbamate [Rivastigmine] 1 g of the oil obtained in Example 4 is dissolved in 10 mL of methanol and 1.4 mL of acetic acid, cooling the mixture between 0C and -5 C. 0.32 g of sodium cyanoborohydride are added to this mixture, maintaining the temperature under 0C. Once the addition has been completed, 0.53 mL of a 37% formaldehyde aqueous solution in 10 mL of methanol are added and it is maintained stirring at room temperature until the end of the reaction. Then 10 mL of a 10% hydrochloric acid aqueous solution are added, the methanol residues are distilled at reduced pressure and extracted with 10 mL of methylene chloride. 20 mL of methylene chloride are added to the separated aqueous phase and the mixture is adjusted to pH 8.7 with sodium hydroxide aqueous solution. The separated organic phase is distilled at reduced pressure until obtaining a yellow oil weighing 0.8 g, and which is identified as the desired product. 1H NMR: delta 1.15-1.2 (2*t, 3H, N-CH2-CH3) ; delta 1.3 (d, 3H, -CH-CH3) ; delta 2.2 (s, 6H, N-CH3); delta 2.96- 3.04 (2*s, 3H, OCN-CH3); 3.2 (q, 1H, -CH-CH3) ; delta 3.36-3. 44 (2*q, 2H, N-CH2-CH3) ; delta 6.96 (d, 1H, Ar-H); delta 7.05 (s, 1H, Ar-H); delta 7.10 (d, 1H, Ar-H); delta 7.3 (t, 1H, Ar-H)
 

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