Bazinaprine CAS 94011-82-2

Introduction：Basic information about Bazinaprine CAS 94011-82-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Bazinaprine Basic information

• Product Name: Bazinaprine
• Synonyms: Bazinaprine;SR 95191;3-[[2-(Morpholin-4-y1)ethyl]amino]-6-phenyl-4-pyridazinecarbonitrile;3-[(2-Morpholinoethyl)amino]-6-phenyl-4-pyridazinecarbonitrile;3-((2-Morpholinoethyl)aMino)-6-phenylpyridazine-4-carbonitrile;4-Pyridazinecarbonitrile, 3-[[2-(4-morpholinyl)ethyl]amino]-6-phenyl-;Bazinaprine, 10 mM in DMSO
• CAS: 94011-82-2
• MF: C17H19N5O
• MW: 309.37
• Mol File: 94011-82-2.mol

Bazinaprine Chemical Properties

• Boiling point: 589.3±50.0 °C(Predicted)
• density: 1.26±0.1 g/cm3(Predicted)
• storage temp.: 2-8°C
• pka: 6.65±0.10(Predicted)

Bazinaprine Usage And Synthesis

Chemical Properties

Yellow solid, melting point 138°C.
Bazinaprine Dihydrochloride: Ca7H19N5O·2HCl. Crystallizes, melting point 144°C (decomposition).

Originator

SR 95.191,Clin Midy/Sanofi

Uses

Bazinaprine can be used as a monoamine oxidase depressant in the preparation of antipsychotics.

Manufacturing Process

240.25 g of ethyl malonate, 138.0 g of potassium carbonate, 5.0 g ofpotassium iodide and 154.0 g of phenacylchloride in 2 L of anhydrous acetoneare heated under reflux overnight. After the inorganic salts have been filteredoff, the filtrate is evaporated to dryness and the excess ethyl malonate is thendistilled off under reduced pressure (pressure: 0.5 mbar; temperature: about60°C). The distillation residue is chromatographed on a silica column using acyclohexane/ethyl acetate mixture (9:1) as the eluent. The ethylphenacylmalonate is obtained in the form of a red oil. Yield: 80.3%.
40.5 g of the ethyl phenacylmalonate are dissolved in 70 ml of absoluteethanol, and 7.25 g of hydrazine hydrate are added dropwise to the reactionmedium at 0°C, with stirring. When the reaction medium has returned toroom temperature, it is stirred for 24 h and the beige precipitate obtained,which corresponds to the expected pyridazinone, is then filtered off. Thefiltrate is treated with 3.62 g of hydrazine hydrate. After stirring for 24 h, anadditional quantity of pyridazinone can be filtered off. The same operation isrepeated once more on the filtrate. After purification by passage through asilica column using a cyclohexane/ethyl acetate mixture (1:1) as the eluent,the 4-ethoxycarbonyl-6-phenyl-4,5-dihydro-2H-pyridazin-3-one is obtained.Yield: 37%.
9.0 g of the 4-ethoxycarbonyl-6-phenyl-4,5-dihydro-2H-pyridazin-3-one aredissolved in 200 ml of acetic acid, and 11.18 g of bromine are then added tothe solution, with stirring. Decolouration of the medium occurs after 5 min.After 2 h at room temperature, and with stirring, the medium is poured into200 ml of water, the mixture is then extracted with methylene chloride andthe organic phase is evaporated to dryness. The residue is taken up 3 timeswith cyclohexane. The beige powder obtained is chromatographed on a silicacolumn using a cyclohexane/ethyl acetate mixture (1:1) as the eluent. The 4-ethoxycarbonyl-6-phenyl-2H-pyridazin-3-one, melting point 150°C is obtained.Yield: 51%.
2.0 g of the 4-ethoxycarbonyl-6-phenyl-2H-pyridazin-3-one are added to 40ml of concentrated ammonia solution and the mixture is stirred overnight atroom temperature. The solid is filtered off and dried to give the 6-phenyl-3-oxo-2H-pyridazine-4-carboxamide, melting point >300°C. Yield: 86%.1.5 g of the 6-phenyl-3-oxo-2H-pyridazine-4-carboxamide are dissolved in 20ml of phosphorus oxychloride and the solution is then heated at 80°C for 5 h.The mixture is poured into 50 ml of water. A precipitate appears, which isfiltered off and dried. There are obtained 58.3% of 3-chloro-4-cyano-6-phenylpyridazine, melting point 206°C.
7.3 g of the 3-chloro-4-cyano-6-phenylpyridazine are dissolved in 60 ml of nbutanol,and 8.0 g of N-(2-aminoethyl)-morpholine are added. The mixture isheated under reflux for 3 h and then poured into 1000 ml of water. Theorganic phase is extracted with ether and the ether solution is then extractedwith a 1 N solution of sulfuric acid. The aqueous phase is separated off,rendered alkaline with sodium hydroxide and extracted with ether. The etherphase is dried over magnesium sulfate and the solvent is then evaporated offto dryness in vacuo to give Bazinaprine, as yellow solid, melting point 138°C. Yield: 81.3%.

Therapeutic Function

Antidepressant

Bazinaprine Preparation Products And Raw materials

• Raw materials: Pyridazine-->Ammonia-->Sulfuric acid-->2-Chloroacetophenone-->Diethyl malonate-->Sodium hydroxide-->Acetic acid-->Hydrazine hydrate-->Potassium carbonate-->Phosphorus oxychloride-->4-(2-Aminoethyl)morpholine-->Potassium iodide-->Phosphorus oxitrichloride