1-(2,3,4-Trimethoxy-benzyl)-piperazine

Base Information

• Chemical Name: 1-(2,3,4-Trimethoxy-benzyl)-piperazine
• CAS No.: 13171-25-0
• Molecular Formula: C₁₄H₂₂N₂O₃*2ClH
• Molecular Weight: 339.262
• Hs Code.: 29339900
• NSC Number: 759317
• ChEMBL ID: CHEMBL1476337
• Mol file: 13171-25-0.mol

Synonyms:Trimetazidine DiHCl;MLS001240268;1-(2,3,4-Trimethoxy-benzyl)-piperazine;SMR000674573;MLS002153871;SCHEMBL348591;CHEMBL1476337;Pharmakon1600-01506088;NSC759317;AKOS026260683

Chemical Property of 1-(2,3,4-Trimethoxy-benzyl)-piperazine

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 1.73E-05mmHg at 25°C
• Melting Point: 231-235 °C
• Boiling Point: 364 °C at 760 mmHg
• Flash Point: 174 °C
• PSA: 42.96000
• LogP: 2.98830
• Storage Temp.: Refrigerator
• Solubility.: Freely soluble in water, sparingly soluble in alcohol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 302.1397203
• Heavy Atom Count: 20
• Complexity: 259

Purity/Quality:

99% ^*data from raw suppliers

Trimetazidine dihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=C(C=C1)CN2CCNCC2)OC)OC.Cl
• Description: Trimetazidine dihydrochloride is the dihydrochloride salt of Trimetazidine. It is a drug used for the treatment of angina pectoris. It is capable of improving the left ventricular function in diabetic patients suffering coronary heart disease as well as treating the symptoms of patients suffering heart failure of different etiologies. It takes effects through acting as an anti- ischemic metabolic agent being capable of improving the utilization efficiency of myocardial glucose by inhibiting the metabolism of fatty acid (through inhibiting the activity of mitochondrial long- chain 3-ketoacyl coenzyme A Thiolase). The shift from fatty acid oxidation to glucose oxidation optimizes cellular energy process in cells exposed to hypoxia or ischaemia, further maintaining the intracellular ATP levels and ensuring the normal function of ionic pumps and transmembrane sodium-potassium flow to maintain cellular homeostasis. Trimetazidine (hydrochloride) (Item No. 18165) is an analytical reference standard that is structurally categorized as a piperazine. It decreases fatty acid β-oxidation by reversibly inhibiting mitochondrial long-chain 3-ketoacyl thiolase (IC50 = 75 nM). This, in turn, stimulates glucose oxidation. In ischemic heart, trimetazidine reduces ischemia/reperfusion injury in clinical trials. Compounds that reduce mitochondrial fatty acid β-oxidation, including trimetazidine, have shown clinical efficacy against chronic stable angina in clinical trials. In part because of its ability to ameliorate testosterone cardiotoxicity, trimetazidine has been classified as a prohibited substance by the World Anti-Doping Agency. This product is intended for research and forensic applications.
• Uses: Antianoxic 1-(2,3,4-Trimethoxybenzyl)piperazine dihydrochloride or trimetazidine dihydrochloride can be used as a building block to synthesize: Phenylpropyl trimetazidine derivatives with potent cerebral vasodilator activity.Benzoylguanidine-trimetazidine derivatives for myocardial ischemic-reperfusion activity studies. Coronary vasodilator. Antianginal

Technology Process of 1-(2,3,4-Trimethoxy-benzyl)-piperazine

There total 1 articles about 1-(2,3,4-Trimethoxy-benzyl)-piperazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

piperazine (110-85-0) + 2,3,4-trimethoxybenzaldehyde (2103-57-3) → trimetazidine dihydrochloride (13171-25-0,127881-54-3)

Guidance literature:

piperazine; With acetic acid; In methanol; at 40 ℃; for 0.5h;

2,3,4-trimethoxybenzaldehyde; With hydrogen; cetyltrimethylammonim bromide; nickel; In methanol; at 35 - 60 ℃; for 4h; under 3750.38 - 6000.6 Torr; Sealed tube;

With hydrogenchloride; In water; for 0.5h; pH=2; Concentration;

Reference yield: 98.0%

chloroacetic acid pyrrolidide (20266-00-6) + trimetazidine dihydrochloride (13171-25-0,127881-54-3) → 1-(pyrrolidinocarbonylmethyl)-4-(2,3,4-trimethoxybenzyl)piperazine (113743-20-7)

Guidance literature:

With potassium carbonate; In acetonitrile; at 70 ℃;

DOI:10.1248/cpb.36.3948

Reference yield: 95.0%

trimetazidine dihydrochloride (13171-25-0,127881-54-3) + 2-Chloro-N,N-diethylacetamide (2315-36-8) → N,N-Diethyl-2-[4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-acetamide (119963-52-9)

Guidance literature:

With potassium carbonate; In acetonitrile; at 70 ℃;

DOI:10.1248/cpb.36.3948

upstream raw materials:

piperazine

2,3,4-trimethoxybenzaldehyde

Downstream raw materials:

1-<2-(pyrrolidino)ethyl>-4-(2,3,4-trimethoxybenzyl)piperazine

1-((E)-3-Phenyl-allyl)-4-(2,3,4-trimethoxy-benzyl)-piperazine; hydrochloride

1-(pyrrolidinocarbonylmethyl)-4-(2,3,4-trimethoxybenzyl)piperazine

1-Piperidin-1-yl-2-[4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-ethanone

Refernces

• 1、 -. "Method for preparing trimetazidine dihydrochloride". Paragraph 0027; 0028; 0029; 0030; 0031. . Retrieved 2017/07/11.