34661-75-1

Basic information

• Product Name: 6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil
• Synonyms: 1,3-dimethyl-6-(3-(4-(o-methoxyphenyl)-1-piperazinyl)proppylamino)-uraci;6-(3-(4-(o-methoxyphenyl)-1-piperazinyl)propylamino)-1,3-dimethyluracil;b-66256;ebrantil;URAPIDIL;6-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil;UrapidilC20H29N503;URAPIDIL [6-((3-(4-(2-METHOXYPHENYL)-1-PIPERAZINYL)PROPYL)AMINO)-1,3-DIMETHYLURACIL]
• CAS NO: 34661-75-1
• Molecular Formula: C₂₀H₂₉N₅O₃
• Molecular Weight: 387.48
• EINECS: 252-130-4
• Product Categories: API's;API;EBRANTIL
• Mol File: 34661-75-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 156-158°
• Boiling Point: 513.42°C (rough estimate)
• Flash Point: 285.8 °C
• Appearance: /
• Density: 1.2058 (rough estimate)
• Vapor Pressure: 4.22E-12mmHg at 25°C
• Refractive Index: 1.7600 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.10(at 25℃)
• Merck: 14,9865
• CAS DataBase Reference: 6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil(34661-75-1)
• EPA Substance Registry System: 6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil(34661-75-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• RTECS: YQ9862000
• Hazardous Substances Data: 34661-75-1(Hazardous Substances Data)

Usage

Description

6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil is a complex organic compound with a unique chemical structure. It is characterized by its uracil core, which is modified with various functional groups, including a piperazinylpropyl chain and a methoxyphenyl group. This molecule exhibits a range of biological activities and has potential applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil is used as an active pharmaceutical ingredient (API) for the development of antihypertensive drugs. It is particularly effective in the treatment of hypertensive emergencies and urgencies, providing rapid and effective blood pressure control.
Used in Research and Development:
6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil is also utilized in research and development for the discovery of new therapeutic agents. Its unique structure and biological activities make it a valuable tool for studying various physiological processes and identifying potential targets for drug intervention.
Used in Drug Formulation:
6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil is used in the preparation of Urapidil Hydrochloride crystal, which is a specific formulation of the compound with improved solubility and stability. This formulation is particularly useful for the development of pharmaceutical products with enhanced bioavailability and efficacy.
Used in Medical Diagnostics:
In addition to its therapeutic applications, 6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil may also be employed in the development of diagnostic tools and tests. Its unique chemical properties and interactions with biological systems can be leveraged to create sensitive and specific diagnostic assays for various medical conditions.
Used in Italian Emergency and Intensive Care Departments:
6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil is used as an antihypertensive agent in Italian emergency and intensive care departments. It is particularly valuable in these settings due to its rapid onset of action and ability to effectively manage severe hypertension in critically ill patients.

Originator

Ebrantil,Byk Gulden,W. Germany,1978

Manufacturing Process

20.6 g (0.083 mol) of N-(o-methoxyphenyl)-N'-(3-aminopropyl)-piperazine and 15.7 g (0.09 mol) of 1,3-dimethyl-4-chlorouracil were boiled for 15 hours in 100 ml triethylamine. The excess triethylamine was then distilled off in vacuo and the residue was dissolved in 300 ml 1 N hydrochloric acid with subsequent filtration. The filtrate thus obtained was cooled with ice and 2 N aqueous ammonic solution was slowly added with stirring. As soon as the first precipitation appeared, a few crystals of the desired product were added to the solution. The ammoniacal suspension was stirred for one more hour, the precipitate filtered off by suction and washed with 200 ml water. The material was purified by recrystallization from ethanol with the addition of activated carbon. In this manner 242 g 1,3-dimethyl-4-[γ-[4-(o_x0002_methoxyphenyl]-piperizinyl-(1)]propylamino] uracil having a melting point of 156°C were obtained corresponding to a yield of 75%. The purification may also be effected by boiling the material in acetone to result in similar yields.

Therapeutic Function

Hypotensive

InChI:InChI=1/C20H29N5O3/c1-22-18(15-19(26)23(2)20(22)27)21-9-6-10-24-11-13-25(14-12-24)16-7-4-5-8-17(16)28-3/h4-5,7-8,15,21H,6,9-14H2,1-3H3

Upstream product

• 5464-78-8 1-(2-methoxyphenyl)piperazine hydrochloride 
• 34654-81-4 6?(3?chloropropyl)amino?1,3?dimethyluracil 
• 6972-27-6 1,3-Dimethyl-6-chlorouracil 
• 20529-23-1 3-(4-(2-methoxyphenyl)piperazin-1-yl)propylamine 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 

Downstream Products

• 769-42-6 1,3-dimethylbarbituric acid 
• 20529-23-1 3-(4-(2-methoxyphenyl)piperazin-1-yl)propylamine 
• 96-31-1 N,N'-Dimethylurea 

Relevant articles and documents

New and efficient technique for the synthesis of Urapidil using β-cyclodextrin as an inverse phase-transfer catalyst

A novel and efficient procedure has been developed for the preparation of Urapidil, (6-({3-4-(2-methoxyphenyl) piperazin-1-yl] propyl} amino)-1,3-dimethyl pyrimidine-2,4-(1H, 3H)-dione), from 6-[(3-chloropropyl) amino]-1, 3-dimethyluracil and 1-(2-methoxyphenyl) piperazine hydrochloride under inverse phase-transfer catalysis (IPTC) conditions. To optimize the reaction conditions, the alkylation reaction was carried out with a range of inverse phase-transfer catalysts, agitation speeds, reaction times, reaction temperatures, mole ratios and catalyst loadings. In addition, the factors affecting the rate of reaction were studied and the rate constant obtained is consistent with the pseudo-first order rate equation. When β-cyclodextrin was used as a catalyst, Urapidil was obtained as a white crystalline powder in 82.6% isolated yield with 99.6% purity after 2-3 h reaction in alkaline aqueous media at 95°C with an agitation rate of 1500 rpm.

New method for preparing urapidil

The invention relates to a new preparation method of urapidil hydrochloride. The method takes 3-[4-(2-methoxyphenyl)piperazine-1-yl]propylamine and 6-chloro-1,3-dimethyluracil as intermediates to prepare urapidil, and then urapidil hydrochloride is obtained by salifying. The new preparation technology of urapidil hydrochloride is characterized in that the raw material structure is simple, water isadopted as a solvent, post-treatment is easy, the product purity is high, the total weight of related substances is less than 0.3%, the yield is high, the total yield is higher than 79%, and the preparation technology is suitable for industrialized production.

Synthesis and physico chemical properties of the antihypertensive agent urapidil

6-{3-[4-(o-Methoxyphenyl)-1-piperazinyl]-propylamino}-1,3-dimethyluracil (Urapidil, Ebrantil) is a new antihypertensive agent whose synthesis and physico-chemical properties are described. The size of the permeation constant K(D) of the passive transport through collodion-lecithin membranes and the value of the partition coefficient P in the neutral area indicate a good absorption and uniform distribution of the substance in the organism.