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Chemical Structure| 105601-20-5 Chemical Structure| 105601-20-5

Structure of 105601-20-5

Chemical Structure| 105601-20-5

3-[1-(Dimethylamino)ethyl]phenyl Ethyl(methyl)carbamate

CAS No.: 105601-20-5

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Cat. No.: A686088 Purity: 95+%

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Product Details of [ 105601-20-5 ]

CAS No. :105601-20-5
Formula : C14H22N2O2
M.W : 250.34
SMILES Code : O=C(OC1=CC=CC(C(N(C)C)C)=C1)N(CC)C
MDL No. :MFCD09832922

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Application In Synthesis of [ 105601-20-5 ]

* 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 [ 105601-20-5 ]

[ 105601-20-5 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 42252-34-6 ]
  • [ 105601-04-5 ]
  • [ 105601-20-5 ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate; In acetonitrile; at 70 - 80℃; Condensation reaction of 3-(l-dimethylaminoethyl) phenol (10 gm) and ethylmethylcarbamoyl chloride (10gm) was carried in the presence of potassium carbonate (25 gm) and acetonitrile (150 ml) at 70-80 C. After completion of reaction, the reaction mixture was quenched in water (250 ml) at 30-35 C and extracted in ethyl acetate (100ml). Evaporation of ethyl acetate gave the desired compound in 70% yield. Yield: 80-85 gms. %Yield: 66.0% HPLC Purity: 99%.
b) Preparation of 3-(1-(dimethylamino)ethyl)phenyl ethyl-(methyl) carbamate (rivastigmine base) An amount of 5.25 g (30.0 mmol) of 3-(1-dimethylaminoethyl)-phenol was dissolved in 70 ml of acetonitrile. To the solution was slowly added 1.30 g (32.5 mmol) of sodium hydride and stirred for 30 minutes. 6.20 g (51 mmol) of ethyl(methyl)-carbamic chloride were slowly added to the solution. The reaction mixture was stirred for 20 hours. The mixture was filtered and concentrated. 100 ml of water were added and the pH was adjusted with 0.1 M NaOH to pH 12, followed by extraction with ether (3x100 ml). The organic layer was then washed with 100 ml of brine, dried over sodium sulfate, filtered and concentrated. 6.20 g of an oily residue of rivastigmine base were obtained.
An amount of 1.1 g (27.5 mmol, 60 %, 1.05 mole) of sodium hydride suspended in 15 ml of acetonitrile was added to 1.0 mole of the above obtained 3-(1-dimethylaminoethyl)phenol (as acetonitrile solution) within a period of 30 minutes while maintaining the reaction mixture at the room temperature. After the addition of sodium hydride an amount of 3.1 ml (3.44 g, 97 % 27.5 mmol, 1.05 molar equivalent) of ethyl(methyl)-carbamic chloride were added within a period of 30 minutes. The reaction mixture was stirred for 2 hours at room temperature and then the solvent was removed under vacuum at 50 mbar and 50C. 55 ml of ether and 35 ml of water were added to the residue, the pH was set to 11 with 0.1 M NaOH and stirred for 20 minutes. The layers were separated. The water phase was washed with 25 ml of ether and the organic phases were combined, dried with 2.0 g of Na2SO4 and filtered. The filtrate was concentrated to obtain 6.4 g of an oily substance of 3-(1-(dimethylamino)ethyl)phenyl ethyl(methyl)carbamate. Yield from 1-(3-hydroxyphenyl)-N,N-dimethyl-ethanaminium chloride was 85 %, purity of the product 97.7 area %.
  • 2
  • [ 90870-20-5 ]
  • [ 105601-04-5 ]
  • [ 105601-20-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In dimethyl sulfoxide; at 90 - 110℃; for 35 - 40h; 3- (1-dimethylaminoethyl) phenol (200gm, 1.21 moles), anhydrous potassium carbonate (252gm, 1.515 moles), N-ethyl-N-methyl-4-nitrophenyl carbamate (340gm, 1.82 moles) and dimethylsulfoxide [(1] liter) are mixed and heated at a temperature of about [90] to about [110C,] under nitrogen atmosphere, for 35-40 hours. The reaction mixture is cooled gradually to room temperature and filtered. The filtered solution is quenched in ice-water mixture and extracted with ethyl acetate to furnish racemic Rivastigmine.
  • 3
  • [ 624-78-2 ]
  • [ 105601-04-5 ]
  • [ 530-62-1 ]
  • [ 105601-20-5 ]
YieldReaction ConditionsOperation in experiment
A mixture of <strong>[105601-04-5]3-[1-(dimethylamino)ethyl]phenol</strong> (0.82 g, 5 mmoL) in acetonitrile (5 mL) was stirred under nitrogen and cooled using an ice-bath. 1,1'-Carbonyldiimidazole (1.0 g, 6 mmoL) was added and the resulting solution was stirred at room temperature for 1.5 h. The solution was re-cooled using an ice-bath and acetic acid (1.0 g, 16.7 mmoL) was added followed by N-ethylmethylamine (0.5 g, 8.3 mmoL). The solution was allowed to warm slowly to room temperature and stirred for 3 hours. The reaction mixture was evaporated and the residue was dissolved in diethyl ether (20 mL). Water (10 mL) was added to the solution and the pH of the aqueous layer was adjusted to >10 by the addition of aqueous NaOH. The organic layer was separated and the aqueous layer was extracted with diethyl ether. The combined organic extracts were washed with water and evaporated to dryness to give racemic Rivastigime (0.8 g) as a liquid.
A mixture of <strong>[105601-04-5]3-[1-(dimethylamino)ethyl]phenol</strong> (0.41 g, 2.5 mmoL) in acetonitrile (5 mL) was stirred under nitrogen at room temperature. 1,1'-Carbonyldiimidazole (0.5 g, 3.0 mmoL) was added to the mixture and the resulting solution was stirred at room temperature for 1.5 h. The solution was cooled using an ice-bath and acetic acid (0.5 g, 8.3 mmoL) was added followed by aqueous 40% N-ethylmethylamine solution (0.6 g, 4 mmoL). The solution was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was evaporated and the residue was dissolved in diethyl ether (15 mL). Water (10 mL) was added to the solution and the pH of the aqueous layer was adjusted to >10 by the addition of aqueous NaOH solution. The organic layer was separated and the aqueous layer was extracted with diethyl ether. The combined ethereal extracts were washed with water and evaporated to dryness to give racemic Rivastigime (0.38 g) as a liquid.
3-(l-dimethylaminoethyl) phenol (10 gm, 0.06 moles) was added to dichloromethane(50ml) followed by addition of carbonyl diimidazole (2Og, 0.123mole). The reaction mass was refluxed for 12 hours and the reaction mass was then cooled to 5-1O0C.Ethylmethyl amine (7.08gms; 2.0 moles) was added to the mixture and stirred for 4-6 hours till completion of reaction. Water (100 ml) was added to quench the reaction. The dichloromethane layer was separated and treated with 10% NaOH solution (50ml) at10-150C. The organic layer was then treated with dilute hydrochloric acid, neutralized with ammonia solution and extracted with Hexane. The hexane layer was concentrated to give compound (I).
  • 4
  • [ 105601-04-5 ]
  • [ 624-60-2 ]
  • [ 530-62-1 ]
  • [ 105601-20-5 ]
YieldReaction ConditionsOperation in experiment
A mixture of <strong>[105601-04-5]3-[1-(dimethylamino)ethyl]phenol</strong> (0.82 g, 5 mmoL) in acetonitrile (5 mL) was stirred under nitrogen and cooled using an ice-bath. 1,1'-Carbonyldiimidazole (1.1 g, 6.8 mmoL) was added and the resulting solution was stirred at room temperature for 2 h. The solution was re-cooled using an ice-bath and acetic acid (0.4 g, 8.3 mmoL) was added followed by N-ethylmethylamine hydrochloride (0.76 g, 10 mmoL) and triethylamine (1.0 g, 10 mmol). The solution was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was evaporated and the residue was dissolved in diethyl ether (20 mL). Water (10 mL) was added to the solution and the pH of the aqueous layer was adjusted to >10 by the addition of aqueous NaOH. The organic layer was separated and the aqueous layer was extracted with diethyl ether. The combined organic extracts were washed with water and evaporated to dryness to give racemic Rivastigime (0.6 g) as a liquid.
  • 5
  • [ 624-78-2 ]
  • [ 105601-04-5 ]
  • [ 7693-46-1 ]
  • [ 105601-20-5 ]
YieldReaction ConditionsOperation in experiment
A solution of <strong>[105601-04-5]3-[1-(dimethylamino)ethyl]phenol</strong> (0.41 g, 2.5 mmoL) and triethylamine (0.8 g, 7.9 mmoL) in dichloromethane (10 mL) was stirred under nitrogen and cooled using an ice-bath. 4-Nitrophenyl chloroformate (0.6 g, 3 mmoL) was added to the solution and the mixture was stirred for 1 h whereupon N-ethylmethylamine (0.24 g, 4 mmoL) was added and the solution was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was quenched by the addition of water (10 mL) and the pH of the aqueous layer was adjusted to >10 by the addition of aqueous NaOH solution. The organic layer was separated and the aqueous layer was extracted with additional dichloromethane. The combined extracts were washed with water and evaporated to dryness. The residue was dissolved in diethyl ether and extracted with dilute HCl solution. The pH of the aqueous solution was adjusted to >10 by the addition of aqueous NaOH and extracted with diethyl ether. The ethereal layers were washed with water and evaporated to dryness to give racemic Rivastigime (0.48 g) as a liquid.
  • 6
  • [ 624-78-2 ]
  • [ 50893-53-3 ]
  • [ 105601-04-5 ]
  • [ 105601-20-5 ]
YieldReaction ConditionsOperation in experiment
A solution of <strong>[105601-04-5]3-[1-(dimethylamino)ethyl]phenol</strong> (0.41 g, 2.5 mmoL) and triethylamine (0.8 g, 7.9 mmoL) in dichloromethane (10 mL) was stirred under nitrogen and cooled using an ice-bath. 1-Chloroethyl chloroformate (0.43 g, 3 mmoL) was added to the solution and the mixture was stirred for 1 h whereupon N-ethylmethylamine (0.24 g, 4 mmoL) was added and the solution was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was quenched by the addition of water (10 mL) and the pH of the aqueous layer was adjusted to >10 by the addition of aqueous NaOH solution. The organic layer was separated and the aqueous layer was extracted with additional dichloromethane. The combined organic extracts were washed with water and evaporated to dryness. The residue was dissolved in diethyl ether and extracted with dilute HCl solution. The pH of the aqueous solution was adjusted to >10 by the addition of aqueous NaOH solution and extracted with diethyl ether. The ethereal layers were washed with water and then evaporated to dryness to give racemic Rivastigime (0.5 g) as a liquid.
  • 7
  • [ 105601-20-5 ]
  • (R)-3-(1-(dimethylamino)ethyl) phenylethyl(methyl)carbamate [ No CAS ]
  • [ 123441-03-2 ]
 

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