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[ CAS No. 93413-61-7 ] {[proInfo.proName]}

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Chemical Structure| 93413-61-7
Chemical Structure| 93413-61-7
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Product Details of [ 93413-61-7 ]

CAS No. :93413-61-7 MDL No. :MFCD13185975
Formula : C23H31NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 353.50 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 93413-61-7 ]

* 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 [ 93413-61-7 ]

[ 93413-61-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 93413-61-7 ]
  • [ 5664-33-5 ]
  • [ 93413-62-8 ]
YieldReaction ConditionsOperation in experiment
palladium-carbon; In ethanol; Hydrogenolysis of this product to remove the benzyl protecting group from the 4-hydroxyphenyl moiety was accomplished by dissolving 1.0 grams of the product in 100 ml. ethanol. One gram, 10% Pd/C was introduced followed by cyclohexa-1,4-dienone (5 ml.). The mixture was stirred for ninety minutes at ambient temperature. The catalyst was removed by filtration and the solvent removed by evaporation to yield 800 mg. of solid.
  • 2
  • [ 93413-61-7 ]
  • [ 93413-62-8 ]
YieldReaction ConditionsOperation in experiment
98% Concentrated hydrochloric acid is added to the suspension until pH 5 is obtained. Raney nickel washed with methanol (9.75 g) is added to the resulting solution and the mixture is heated to 50 0C under intensive stirring. The mixture is hydrogenated with gaseous hydrogen at the atmospheric pressure (0.1 MPa) for 2 hours. The mixture is then filtered through diatomaceous earth. The pH value of filtrate is adjusted to 9.5 by dropwise addition of a 25% aqueous solution of ammonia. The suspension is then stirred at a laboratory temperature for 1 hour and then filtered. The filtration cake is washed with water and dried. Yield 28.5 g (98 %), HPLC purity 99.7%.
95% With formic acid; hydrogen;1% Pd/C; In methanol; at 30℃; under 750.075 Torr; for 6h;pH 5;Inert atmosphere;Product distribution / selectivity; Example 3: Preparation of desvenlafaxine base (I)O-Benzyl desvenlafaxine (II, R = H) base (70 g) is stirred up in methanol (400 ml) and formic acid (12 ml) is added dropwise. 10% Pd/C (2 g) is added to the solution. Gaseous hydrogen is bubbled through the mixture at the atmospheric pressure (0.1 MPa) at 30 C for 6 hours. pH of the solution is adjusted to 5 by addition of formic acid. The mixture is filtered through kieselguhr. The pH value of the filtrate is adjusted to 9.5 by dropwise addition of 25% aqueous solution of ammonia. Then, the suspension is stirred at the laboratory temperature for 1 hour and then filtered. The filter cake is washed with water and dried. Yield 50 g (95%), HPLC purity 99.6%.
95% With ammonium formate;1% Pd/C; In methanol; at 60℃; for 2h;Product distribution / selectivity; Example 1 : Preparation of desvenlafaxine base0-Benzyldes venlafaxine base (35 g) is stirred up in MeOH (300 ml). Ammonium formate (25 g) and 3% Pd/C (3.5 g) are added to the solution. The mixture is stirred at 60 C for 2 hours. The pH of the reaction mixture is adjusted to 5 by addition of formic acid. The mixture is filtered through kieselguhr. The pH value of the filtrate is adjusted to 9.5 by dropwise addition of a 25% aqueous solution of ammonia. The suspension is then stirred at the laboratory temperature for 1 hour and then filtered. The filter cake is washed with water and dried. Yield 25 g (95 %); HPLC purity 99.4 %.
87% With hydrogen;palladium on carbon; In ethanol; at 25℃; under 760.051 Torr; Amine (V) (2g) was debenzylated in the presence of hydrogen gas over 20% Pd/C (0.2g, 10%w/w) in ethanol (50ml) at atmospheric pressure and at 25C. After completion of the reaction, the mixture was filtered through Celite to remove catalyst. The filtrate was concentrated to obtain a residue. Hexane (50ml) was added to the residue and stirred for 30 minutes. It was then filtered to obtain ODV free base (I) as an off-white solid. The structure of the product was confirmed by 1H-NMR. Weight of the product = 1.3g; molar yield = 87%.
87.24% With hydrogen;palladium 10% on activated carbon; In ethanol; toluene; at 25℃; under 7757.43 Torr; for 4h; 1-[1-(4-benzyloxy-phenyl)-2-dimethylamino-ethyl]-cyclohexanol (2 gm; 0.006 mol) was debenzylated in the presence of hydrogen gas over 10% Pd/C (0.4 gm) in specially purified denatures spirit (SPDS)-toluene (50 ml) under 150 psi pressure and at 25C for about 4.0 hours. After completion of the reaction, catalyst was removed by filtration, the filtrate was concentrated to obtain residue. Ethyl acetate (10 ml) was added to the residue, stirred for 30 minutes at 50cC and further stirred for 30 min to 1 hour at room temperature. The solid was isolated by filtration to obtain ODV (1.3 g, 0.005 mol) as an off-white crystalline solid. Efficiency: 87.24%.
81.08% With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 6h; Examplc-8; Preparation of l-r2-(dimemylamitioVl-r4-hvdroxyphenv?ethyl]cvclohexanol (O- desmethylvenlafaxine); l-[2-(Dimethylamino)-l-(4-benzyloxyrhohenyl) ethyl] cyclohexanol ( 30 g) was dissolved in methanol ( 600 ml), charged with 10% palladium on carbon (3 g) and hydrogenated pressure for 6 h at room temperature. The catalyst was filtered, washed with methanol, and combined filtrate evaporated under reduced pressure to give 18g (81.08%) of the l-[2-(dimetihylaniino)-l-(4-hydroxyphenyl)ethyl]cyclohexanol.
81% With sodium sulfide; In 1-methyl-pyrrolidin-2-one; at 145℃; for 12h;Inert atmosphere; Under nitrogen, 23.4 g of anhydrous sodium sulfide, 50 ml of N-methylpyrrolidone was added to the three-necked flask, heated to 145 ± 3 C with stirring, and then 17.68 g of 1- (4- (benzyloxy) Yl) -2- (dimethylamino) -ethyl) -cyclohexanol; the mixture was reacted at 145 C under a nitrogen atmosphere. The reaction was stirred for 12 hours and then allowed to cool to room temperature. The mixture was added with 290 ml of ethyl acetate and 200 ml of water.The mixture was cooled (below 0 C) for overnight, solidified, filtered and dried to give 10.97 g of de-methyllafaxine.
60 g With palladium 10% on activated carbon; hydrogen; In methanol; at 20 - 45℃; Example 1 : Preparation of Desvenlafaxine succinate l-[2-(DimethyIamino)-l-(4-benzyloxyphenyl)ethyl]cyclohexanol ( 1 10 gm), methanol (2200 ml) and palladium carbon (10%, 1 1 gm) were added at room temperature and then heated to 45C. To the reaction mass was applied hydrogen gas for 3 to 4 hours and then cooled to 30C. To the reaction mass was added ethyl acetate (1320 ml) and filtered through hi-flow bed. The solvent was distilled off from the filtrate thus obtained and then added isopropyl alcohol (220 ml). The contents were stirred for 2 hours at 0 to 5C, filtered and then dried to obtain 60 gm of desvenlafaxine.

  • 3
  • [ 919475-15-3 ]
  • [ 108-94-1 ]
  • [ 93413-61-7 ]
YieldReaction ConditionsOperation in experiment
In certain embodiments, the following procedure was employed. 150 g of 2-(4- benzyloxy)phenyl-N,N-dimethylacetamide, 945 g (1062 mL) of THF was charged to a 5 L jacketed reactor. 550 mL of isopropylmagnesium chloride (2.0 M in tetrahydrofuran) was added and the mixture was stirred for 1 h. 115 g of cyclohexanone was added to the reactor and mixed for 1 h. 360 g of RedAI (sodium bis(2-methoxyethoxy)aluminum hydride-65percent w/w in toluene) was added to the reactor and stirred for 16 h. When the reaction was complete the mixture was- 66 -LAI-2932341vl <n="69"/>added to 2005 g of 22percent w/w aqueous citric acid. 420 g (600 mL) of heptane was charged to the reactor and stirred for 15 min. The stirring was stopped and the top layer was removed. 250 g of 50percent NaOH was added to adjust the pH to 9-10, followed by stirring. 1114 g (1500 mL) of MTBE was added to the reactor. The mixture was warmed to 45 +/- 5°C to dissolve the solids. The stirring was stopped and the bottom layer was removed. The organic layer was washed twice with 750 g of water at 450C. 750 mL of MTBE was removed by distillation and 750 mL of methanol was added. About 750 mL of MTBE/methanol was removed by distillation and 300 g of methanol and 300 g of water were added. The slurry was cooled to 0 0C and stirred for 30 min. The slurry was filtered and the solid washed with 375 g of (4:1 methanohwater). The solid was dried to yield 161 g of 1-(2-(dimethylamino)-1-(4-benzyloxyphenyl)ethyl) cyclohexanol.[00261] In certain embodiments, the following procedure was employed. To a 200 gallon reactor was charged 22.98 kg of 2-(4-benzyloxy)phenyl-N,N-acetamide and 145.1 kg of THF. With agitation, the temperature was adjusted to 5 0C to 10 0C. To the reactor was charged 82.9 kg of isopropylmagnesium chloride, 2.0M in THF, while maintaining the temperature between 5 0C to 35 0C. The lines were rinsed with 2.78 kg of THF. The contents were agitated for 61 minutes at 10 0C to 20 0C. To the reactor was added 9.31 kg of cyclohexanone while maintaining the temperature between 5 0C to 35 0C. The lines were rinsed with 2.77 kg of THF. The temperature was adjusted to 15 0C to 25 0C and the contents were agitated for 17 minutes at this temperature range after which the reaction was complete. To the reactor was charged 55.8 kg of sodium bis(2-methoxyethoxy)aluminum hydride (65 wtpercent in toluene) while maintaining the temperature at 15 0C to 35 0C. The contents were agitated for 10 h (<3percent starting material remained). The reaction mixture was added to 334.1 kg of 22percent citric acid solution cooled to 0 0C to 2 °C. THF (22.9 kg) and n-heptane (63.3 kg) were added to the reaction. The mixture was agitated for 15 minutes then the stirring was stopped and the phases were allowed to separate. The top layer was removed and the reactor was charged with 45.4 kg of 50percent sodium hydroxide. The reactor was charged 169.9 kg of MTBE and the temperature was adjusted to 40-50 0C. The contents were agitated for 14 minutes and the agitation was stopped to allow the phases to separate for 15 minutes. The aqueous layer was removed and 115 L of USP purified water was added. The temperature was adjusted to 40 0C to 50 0C. The contents were agitated for 15 minutes and the agitation was stopped to allow the phases to separate for 13 minutes. The aqueous bottom layer was removed. The reactor was charged with 115 L of USP purified water and the temperature was adjusted to 40 0C to 50 0C. The contents were agitated for 15 minutes and the agitation was stopped to allow the phases to separate. The aqueous bottom layer was removed. The solution was distilled under vacuum to a final volume of 188 L. To the reactor- 67 -LAI-2932341vl <n="70"/>was charged 115.2 kg of methanol and the solution was distilled under vacuum to a final volume of 131 L. To the reactor was charged 46.0 kg of methanol and 57 L of USP purified water. The temperature was adjusted to 0 0C. The slurry was stirred for 41 minutes at -5 0C to 5 CC and the mixture was filtered. The cake was washed with 46.2 kg of methanol and 11.6 kg of USP purified water (cooled to -5 0C to 5 0C). The wet cake (30.66 kg) was dried at 40-50 0C to yield 24.47 kg of 1-(2-(dimethylamino)-1-(4-benzyloxyphenyl)ethyl)cyclohexanol.
  • 4
  • [ 6547-53-1 ]
  • [ 93413-61-7 ]
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