Tag: M.W=300-400

103146-25-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Experiment 37: Experiment 11 was repeated except that a mixture of 1-propanol and ethanol (50:50) was used as the solvent in stead of 1-propanol in a total volume of 4.4 V, 0.5 eq of (+)-O,O’-di-/?-toluoyl-(S,S)-tartaric acid was used, and the holding time before filtration was 0.5 h. Molar yield: 27.4%, enantiomeric purity: 99.4% S.

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Reference:
Patent; H. LUNDBECK A/S; WO2009/33488; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 103146-25-4

Oxalate [(+-)-Diol Oxalate Salt] (+-)-Diol compound (VI) (7 g, 0.0205 mol) and oxalic acid dihydrate (2.83 g, 0.0225 ml) were added to isopropyl alcohol (77 ml) and heated the contents to 75-80 C. to obtain a clear solution. The obtained solution was cooled to 10-15 C. and stirred for 2 h to complete the crystallization. The product was filtered, and thereafter dried at 50-60 C. under reduced pressure for 6 h to give 8.6 g of diol oxalate salt (VIa), with HPLC purity of 99.94%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103146-25-4, its application will become more common.

Reference:
Patent; Kaushik, Vipin Kumar; Mohammed, Umar Khan; Meenakshisunderam, Sivakumaran; US2009/99375; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., 103146-25-4

To a stirred solution [OF RACEMIC 4- [4-DIMETHYLAMINO-1- (4-FLUORO-PHENYL)-1-HYDROXY-] [BUTYL]-3-HYDROXYMETHYL-BENZONITRILE] (0,29 mmol, 100 mg) and vinylbutyrate (0,29 mmol, [37 L)] in anhydrous toluene (2,925 ml) is added Novozymes 435, (0,2 mg) and 1,1 eq. Carboxylic acid. The reaction is heated to 40 degrees celcius and followed by HPLC. The enzyme is filtered off and washed with a small amount of toluene. The combined organic phases are evaporated in vacuo and subsequently analyzed on super critical fluid chromatography. Result is shown in table 19.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 103146-25-4.

Example 2 (Preparation of the mixture used in example 1) (S)-4-[4-Dimethylamino-1-(4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethyl- benzonitrile To a stirred solution of racemic 4- [4-Dimethylamino-l- (4-fluorophenyl)-l-hydroxy- butyl] -3-hydroxymethylbenzonitrile (29 mmol, 10 g) and vinylbutyrate (58 mmol, 7,5 ml) in anhydrous 1,4-dioxane (142,5 ml) is added lipoprotein lipase pseudomonas sp. (160 U, 250 mg). The reaction is heated to 50 C and followed by HPLC. After 192 hours at a conversion of 41%, additional 250 mg lipase was added. After 504 hours, at a conversion of 63 % the reaction was stopped. The enzyme is filtered off and washed with a small amount of 1,4-dioxane. The combined organic phases are evaporated in vacuo and subsequently analyzed on super critical fluid chromatography. Obtained ee-value ( (S-diol) = 95% (S-diol/R-diol = 40: 1).

The synthetic route of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2005/77891; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

103146-25-4, Name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 103146-25-4, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

50 gm of 5-Cyano phthalide was stirred in 150 ml of THF at -5C. 227 gm of l-(4-fluorophenyl) magnesium bromide was added to the above solution and stirred for about 15 minutes at -5 0C. 324 gm of l-[3- (dimethylamino) propyl] magnesium chloride was added slowly to the reaction mass at -5 0C and then stirred for about 30 minutes at room temperature. The reaction mixture was quenched into cold water (650 ml). Reaction mixture pH was adjusted to about 2 with 36% aqueous HCl (94 ml) and washed the reaction mixture with toluene (2 X 150 ml). The aqueous layer was separated, toluene (300 ml) was added and pH was adjusted to about 7.5 with aqueous ammonia (45 ml). The organic layer was separated and aqueous layer was extracted with toluene (1 X 200 ml; IX 100 ml). Total organic layer was washed with water (1 X 250 ml) followed by salt solution (1 X 250 ml). The final organic layer was distilled completely under vacuum to get 76 gm of residue.The residue obtained above was charged in 150 ml of toluene, stirred at room temperature for about 1 hour. The solution was cooled to 10-150C and stirred for about 1 hour. The solid was filtered and washed with toluene. The wet solid was dried to get 55 gm of the title compound as crystalline Form S.The obtained product was analyzed by DSC and XRD, the results are as provided in Fig. 1 & 2 respectively.

Statistics shows that 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 103146-25-4.

Reference:
Patent; SHODHANA LABORATORIES LIMITED; GIRIDHAR, Thota; SRINIVASULU, Gudipati; SRINIVASA RAO, Kotaru; WO2010/4575; (2010); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

103146-25-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Experiment 28; Experiment 11 was repeated except that the crystallization mixture did not contain toluene, a mixture of 1-propanol and dichloromethane (85:15) was used as the solvent in stead of 1-propanol in a total volume of 4.5 V, 0.5 eq of (+)-O,O’-di-p-toluoyl-(S,S)-tartaric acid was used, and the holding time before filtration was overnight.Molar yield: 37.8%, enantiomeric purity: 98.8% S.; Experiment 38; A range of experiments were conducted examining the resolution of diol with (+)-(S,S)-DTT. The general procedure is described below, and the details and results for each reaction are in table 1.Racemic diol (20 g, 58.4 mmol) was dissolved in approximately half of the solvent used for the experiment at 40 C. (+)-(S,S)-DTT.H2O (quantity specified in the table) was added as a solution in the other half of the solvent. The solution was held at 40 C. and was seeded within two minutes with crystals of (S)-diol.?(+)-(S,S)-DTT (approximately 5 mg). Crystallization typically began within 5-10 minutes after seeding. After 2 h at 40 C., the temperature of the solution was lowered to 20 C. over 2 h, and the solution was held at this temperature for a further 1 h. The product was then separated by filtration, washed with the appropriate solvent (2¡Á20 mL) and dried overnight at 60 C. under reduced pressure.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; H. Lundbeck A/S; US2009/69582; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding some certain compound to certain chemical reactions, such as: 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 103146-25-4. 103146-25-4

In a 200-ml four-necked flask equipped with a stirrer and a thermometer, 1.5 g [(4.] [38] m mol) of [()-4- [4-DIMETHYLAMINO-1- (4′-FLUOROPHENYL)-1-HYDROXYBUTYL]-3-] hydroxymethylbenzonitrile was dissolved in 30 ml of toluene, then 0.45 g of Novozym 435 (product [OF NOVOZYMES),] 0.347 g (4.38 m mol) of pyridine, 4.38 m mol of various kinds of acids and 1.00 g (8.76 m mol) of vinyl butyrate were added, and stirred at [40C] for between 16 and 21.5 hours. The result is shown in Table 4.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 103146-25-4 as follows. 103146-25-4

R-enriched cyanodiol (I) (lOg, 0.292 moles) prepared as per example 2 was dissolved in dichloromethane (40ml) at 20-40 C and cooled to 0-5C. Then triethylamine (4.4g; 0.043 moles) followed by a solution of benzoyl chloride (4.5g, 0.03 mole) in dichloromethane (10ml) was added at 0-5C. The reaction mass was maintained further at 0-5 C for 2 hours. After maintaining 10% sodium chloride solution was added and the resulting biphasic mixture was stirred at 10- 20 C for 10-20min. Then the organic layer was separated and concentrated under vacuum at 35-40C which afforded 13.2 g of mono benzoyl cyanodiol ester as an oil. To this obtained mono benzoyl cyanodiol ester, acetone (35ml) followed by a solution of oxalic acid dihydrate (3.6g, 0.03rnoles) in acetone (23ml) was added. Then the reaction mass was maintained at 30-40 C for 1-2 hours. After maintaining was over the reaction mass was cooled to 0-5C whereupon the precipitated solid was filtered, washed with acetone (12 ml) and dried under vacuum at 50-60C which afforded 6.0g title compound (lllf) as a white solid. 1H-NMR in CDC13 at 400MHz (ppm): 1.24-1.60 (d, 2H), 2.03-2.31 (d, 2H), 2.48 (s, 6H), 2.79-2.84 (dd, 2H), 4.73-4.77 (d, 1H), 5.27-5.31 (d, 2H), 6.66-7.67 (m, 12H- Aromatic) Mass Analysis (ESI, +ve mode): Molecular ion peak observed at 447.47 a.m.u which corresponds to the freebase of the title compound.

According to the analysis of related databases, 103146-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IPCA LABORATORIES LIMITED; REGURI, Buchi Reddy; PRASAD, Ashok; RAWAT, Ajay Singh; RAJPUT, Sandip; SANTAN, Rohit B; (36 pag.)WO2017/9866; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

103146-25-4, A common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

19.5 g (115.7 mmol) of 48% hydrobromic acid was added dropwise to the solution at 30 C. or lower over 30 minutes. At about 25 C., 60.0 mg (0.18 mmol) of hydrobromide of diol compound (4) was added as a seed crystal and stirred for 30 minutes to confirm crystallization of hydrobromide of diol compound (4). did. Then, it was cooled to around 5 C., and 48.6 g (288.5 mmol) of 48% hydrobromic acid was added dropwise at around 5 C. over 30 minutes. After stirring for 1 hour at around 5 C., the precipitated crystals were separated by centrifugation and washed with 100 mL of water. Further, the crystals were washed with 100 mL of ethyl acetate. The obtained wet body is dried at 40 C. for 15 hours and then dried.118.4 g (279.8 mmol) of hydrobromide of the compound (4) was obtained. The isolated yield of the hydrobromide salt of the diol compound (4) was 97.0% based on the number of moles of the diol compound (4). Moreover, as a result of measuring the obtained hydrobromide salt of the diol compound (4) by HPLC, the purity of the hydrobromide salt of the diol compound (4) was 99.54%. Further, during crystallization of the hydrobromide salt of the diol compound (4), no crystal adhesion (scaling) was observed on the container wall surface.

The synthetic route of 103146-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokuyama Corporation; Miyanoku, Takayuki; Yokoo, Yoshihiro; (12 pag.)JP2019/119710; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts