Category: 1822-51-1

Synthetic Route of 1822-51-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1822-51-1, name is 4-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[00324] A solution of acetyl chloride (6.34 mL, 0.084 mol, 4 equiv) dissolved in anhydrous EtOH (50 mL) was stirred for 0.5 h and added to a solution of homopiperazine (10.4 g, 0.1 mol, 5 equiv) in EtOH (250 mL). The reaction mixture was heated to reflux for 1 h, cooled to 25 C. and a solution of 4-picolyl chloride hydrochloride 93.44 g, 0.021 mol) in EtOH (40 mL) was added. The reaction mixture was heated to reflux for 16 h, cooled to 25 C. and the solvent was removed under vacuum. The residue was diluted with CH2Cl2 (300 mL) and was washed with 2N KOH (1×300 mL). The aqueous layer was extracted with CH2Cl2 (1×300 mL) and the organic phase was washed with 2N KOH (150 mL), dried (MgSO4) and concentrated. Chromatography (SiO2, 5% H2O-5% NH4OH-1PrOH) afforded the desired product (2.88 g, 4.01 g theoretical, 72%) as a yellow oil. TLC Rf 0.45 (5% H2O-5% NH4OH-1PrOH): 1H NMR (CDCl3, 300 MHz) delta 8.77 (d, J=5.9 Hz, 2H), 7.53 (d, J=5.7 Hz, 2H), 3.91 (s, 2H), 3,19 (m, 4H), 2.92 (m, 4H), 2.04 (m, 2H).

According to the analysis of related databases, 1822-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Teijin Intellectual Property Center Limited; Combichem, Inc.; US6686353; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1822-51-1, 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 1822-51-1 as follows.

Example 62: 6-(Pyridin-4-yl-methyl)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl- phenvD-amide; A mixture of 22.4 mg (0.10 mMol) Pd(O2CCH3)2) 52.6 mg (0.20 mMol) triphenylphosphine, 151 mg (0.33 mMol) 6-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-naphthalene-1- carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide and 229.3 mg (1.08 mMol) K3PO4 in 3 ml toluene is degassed repeatedly by evaporation and flushing with N2. Then 59 mg (0.36 mMol) 4-chloromethyl-pyridine hydrochloride are added and the mixture is stirred at 80 0C for 20 h, when additional 18.5 mg (0.082 mMol) Pd(O2CCH3)2 and 43.1 mg (0.164 mMol) triphenylphosphine are added. After 3 h at 110 0C the reaction mixture is poured into water and EtOAc. The aqueous phase is separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography [Combi Flash; CH2CI2 ? CH2CI2/(Me0H + 10 % NH3aq) 9:1] gives the title compound: MS: [M+1]+ = 425; HPLC: AtRe( = 12.7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1822-51-1, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/59234; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1822-51-1 , The common heterocyclic compound, 1822-51-1, name is 4-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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.

Reference Example 1 Methyl 2-(pyridin-4-yl)methoxybenzoate (Reference Compound 1-(1)) To a solution of methyl salicylate (10 g, 66 mmol) and 4-chloromethylpyridine hydrochloride (11 g, 67 mmol) in N,N-dimethylformamide (150 mL) was added potassium carbonate (19 g, 140 mmol) under ice-cooling, and then the mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into an ice water and the aqueous layer was extracted with ethyl acetate (150 mL, twice). The ethyl acetate layer was washed with a saturated brine solution (200 mL), dried over anhydrous sodium sulfate, and concentrated under a reduced pressure to dryness, and the resultant residue was purified with a silica gel column chromatography (hexane/ethyl acetate) and dried to give 12 g (75 %) of the titled compound as a colorless solid. 1H-NMR (300MHz, CDCl3) delta 3.93 (s, 3H), 5.19(s, 2H), 6.97(d, J=8.3Hz, 1H), 7.04(t, J=7.5Hz, 1H), 7.43-7.50(m, 3H), 7.87(dd, J=7.9, 1.8Hz, 1H), 8.63(d, J=6.1Hz, 2H) The following Reference Compounds 1-(2) to (8) were obtained by a production method similar to that of Reference Compound 1-(1) using compounds selected from known compounds, 4-chloromethylquinoline (CAS#5632-17-7;) and 2-acetamido-4-methanesulfonyloxymethylpyridine (CAS#864461-12-1;) and commercially available compounds.

The synthetic route of 1822-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Santen Pharmaceutical Co., Ltd; EP2128156; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1822-51-1, 4-(Chloromethyl)pyridine hydrochloride, 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, Recommanded Product: 1822-51-1, blongs to pyridine-derivatives compound. Recommanded Product: 1822-51-1

To a mixture of diethyl 2-(((3af?,5f?,6/?,daf?)-6-acetoxy-6-ethynyl-2,2-dimethyltetra- hydrofuro[2,3-i/][l,3]dioxol-5-yl)methoxy)malonate (1.2 g, 2.90 mmol, 1 eq) in DMF (20 mL) at 20 C was added CS2CO3 (6.60 g, 20.27 mmol, 7 eq) and 4-(chloromethyl) pyridine hydrochloride (1.90 g, 11.58 mmol, 4 eq). The mixture was stirred for 2 h before it was filtered and the filter cake was washed with EtOAc (20 mL). The filtrate was diluted with water (60 mL) and extracted with EtOAc (3 x 50 mL). The combined extract was washed with water (2 x 50 mL), saturated aq. MLCl (50 mL), brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on S1O2 (14-33% EtOAc in petroleum ether) to give diethyl 2- (((3ciR,5R, 6A*, A/ri>)-6-acetoxy-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-6/][ l ,3]-dioxol-5- yl)methoxy)-2-(pyridin-4-ylmethyl)malonate (900 mg, 61% yield) as a yellow oil

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1822-51-1, 4-(Chloromethyl)pyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; CALITHERA BIOSCIENCES, INC.; CHEN, Lijing; BILLEDEAU, Roland, Joseph; LI, Jim; (437 pag.)WO2019/246403; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1822-51-1, name is 4-(Chloromethyl)pyridine hydrochloride, the common compound, a new synthetic route is introduced below. Product Details of 1822-51-1

EXAMPLE 6; 4-[(R)-2-(4-benzyl-phenoxymethyl)-pyrrolidin-1-ylmethyl]-pyridine; To a solution of Example 1 (0.25 g, 0.82 mmol) in dichloromethane (2 mL) was added 4-picolyl chloride hydrochloride (0.13 g, 0.79 mmol) and triethylamine (0.29 mL, 2.08 mmol). The resulting mixture was stirred at ambient temperature overnight. The crude product was extracted into dichloromethane and washed with water followed by brine. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.11 g, 45%); 1H NMR (400 MHz, CDCl3); delta 1.70-1.81 (m, 3H), 2.03 (m, 1H), 2.27 (m, 1H), 2.94-3.03 (m, 2H), 3.49 (d, J=14.4 Hz, 1H), 3.86 (m, 1H), 3.92 (s, 2H), 3.94 (m, 1H), 4.19 (d, J=14.4 Hz, 1H), 6.79 (d, J=8.8 Hz, 2H), 7.08 (d, J=8.8 Hz, 2H), 7.15-7.20 (m, 3H), 7.26-7.29 (m, 4H), 8.51 (m, 2H); MS (m/z) 359.5 (M+1); LC (99.7%); HPLC (91.6%)

The synthetic route of 1822-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DECODE CHEMISTRY, INC.; US2007/66820; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1822-51-1, Adding some certain compound to certain chemical reactions, such as: 1822-51-1, name is 4-(Chloromethyl)pyridine hydrochloride,molecular formula is C6H7Cl2N, 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 1822-51-1.

A mixture of 4-hydroxylbenzaldehyde (2a) (1.2 g, 10 mmol), 4-(chloromethyl)pyridine hydrochloride (1.6 g, 10 mmol) and K2CO3 (4.2 g, 30 mmol) in dry DMF (12 mL) was stirred at 80 for 7 h. The cooled mixture was extracted with EtOAc (100 mL). The organic layer was washed with brine (2 × 100 mL) , dried (MgSO4) and concentrated to dryness. Yield = 1.3 g (61 %), tan crystals, recrystallised with methanol. m. p. = 102 – 104 (Lit. m. p. 57 – 58 ). TLC: petroleum ether-EtOAc 1: 3 v/v, Rf = 0.24 .1H NMR (DMSO-d6): delta 9.89 (s, 1H, CHO), 8.60 (dd, J = 1.6, 4.5 Hz, 2H, Ar), 7.91 (m, 2H, Ar), 7.47 (d, J = 6.3 Hz, 2H, Ar), 7.22 (dd, J = 1.8, 7Hz, 2H, Ar), 5.33 (s, 2H, CH2).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1822-51-1, 4-(Chloromethyl)pyridine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Taban, Ismail M.; Zhu, Jinge; DeLuca, Hector F.; Simons, Claire; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5629 – 5636;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1822-51-1, 4-(Chloromethyl)pyridine hydrochloride, 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, Computed Properties of C6H7Cl2N, blongs to pyridine-derivatives compound. Computed Properties of C6H7Cl2N

General procedure: Intermediate 9a (or 9b, 0.5 mmol) was dissolved in anhydrous DMF (10 mL) in the presenceof anhydrous K2CO3 (0.14 g, 1 mmol), followed by addition of appropriate substituted benzyl chloride (or 4-picolyl chloride hydrochloride) (0.5 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and water (20 mL) was added. Extracted with ethyl acetate (2 × 10 mL), and the organic phase was washed with saturated sodium chloride solution (10 mL), and dried over anhydrous Na2SO4, which was purified by flash column chromatography to afford title compounds 10a1~a3 and 10b1~b3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1822-51-1, 4-(Chloromethyl)pyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Chen, Xuwang; Liu, Xin; Meng, Qing; Wang, Ding; Liu, Huiqing; De Clercq, Erik; Pannecouque, Christophe; Balzarini, Jan; Liu, Xinyong; Bioorganic and Medicinal Chemistry Letters; vol. 23; 24; (2013); p. 6593 – 6597;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem