N-Octyl-4-pyridinamine

Into 200L reactor was pumped n-octylamine 100kg, 30kg of 4-chloropyridine hydrochloride and 10kg of sodium fluoride were added, the temperature was raised to 130 ° C, and the mixture was stirred for 2 hours while keeping warm, Decompression recovery n-octylamine, while hot sodium carbonate aqueous solution to adjust the pH to about 7, adding ethyl acetate 120kg, separating the aqueous layer, the organic layer was cooled, filtered, Dried to give 4-octylaminopyridine 32.3kg, Purity was 99.3percent, yield was 78.5percent.5.0 g (0.0333 mol) of 4-chlororpyridine hydrochloride, And 0.55 g (0.0333 mol) of n-OCtylaminehydrochloride, The mixture is stirred and heated from 120 ° C to 180 ° C, heated to 200 ° C and held for 7 hours. The reaction was confirmed by thin-layer chromatography, and after completion, it was cooled and cooled to 100 ° C. To the reaction solution was added 20 ml of water and the mixture was cooled with stirring.To the reaction mixture was added 35percent aqueous solution of sodium hydroxide to make it alkaline. The mixture was extracted three times with 20 ml of di-dichloromethane (MC). The organic layer was collected, washed with 10 ml of cold water, washed with saturated brine, dehydrated with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, 14 ml of hexane was added to the residue solid, and the mixture was refluxed and cooled. The resulting crystals were filtered, dried under reduced pressure at room temperature. [0103] 6.4 g of octylaminopyridine base (yield: 93.0percent, MP 65-69 ° C) was obtained through the above-mentioned procedure.Into 200L reactor was pumped n-octylamine 100kg, 30kg of 4-chloropyridine hydrochloride and 10kg of sodium fluoride were added, the temperature was raised to 130 ° C, and the mixture was stirred for 2 hours while keeping warm, Decompression recovery n-octylamine, while hot sodium carbonate aqueous solution to adjust the pH to about 7, adding ethyl acetate 120kg, separating the aqueous layer, the organic layer was cooled, filtered, Dried to give 4-octylaminopyridine 32.3kg, Purity was 99.3percent, yield was 78.5percent.5.0 g (0.0333 mol) of 4-chlororpyridine hydrochloride, And 0.55 g (0.0333 mol) of n-OCtylaminehydrochloride, The mixture is stirred and heated from 120 ° C to 180 ° C, heated to 200 ° C and held for 7 hours. The reaction was confirmed by thin-layer chromatography, and after completion, it was cooled and cooled to 100 ° C. To the reaction solution was added 20 ml of water and the mixture was cooled with stirring.To the reaction mixture was added 35percent aqueous solution of sodium hydroxide to make it alkaline. The mixture was extracted three times with 20 ml of di-dichloromethane (MC). The organic layer was collected, washed with 10 ml of cold water, washed with saturated brine, dehydrated with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, 14 ml of hexane was added to the residue solid, and the mixture was refluxed and cooled. The resulting crystals were filtered, dried under reduced pressure at room temperature. [0103] 6.4 g of octylaminopyridine base (yield: 93.0percent, MP 65-69 ° C) was obtained through the above-mentioned procedure.A. A mixture containing 183.3 g. (0.8 mole) of N-(4-pyridyl)pyridinium chloride hydrochloride and 162 g. (0.98 mole) of n-octylamine hydrochloride was heated in an oil bath to a bath temperature of 225-230 C. (internal temperature of 188 C.) and the resulting liquid was stirred at that temperature for 2.5 hours. The reaction mixture was then cooled to 70 C., diluted with 1 liter of ice and water, made alkaline with 35% aqueous sodium hydroxide and extracted with chloroform. The chloroform extracts were dried over anhydrous sodium sulfate, treated with decolorizing carbon and evaporated to dryness under vacuum. The resulting oil was cooled to -78 C. The semi-solid which formed was triturated with ether and the solid thus-obtained collected by filtration, washed with cold ether and dried. The filtrate afforded a second crop of 10 g. The crops were combined, dissolved in chloroform and, following treatment with decolorizing carbon and filtration (repeated 3 times), the chloroform solution was evaporated to dryness under reduced pressure. The resulting solid was triturated with ether, cooled, collected by filtration and washed with cold ether-hexane to give 63.3 g. or nearly colorless 4-(octylamino)pyridine, m.p. 62-63 C.4-OAP was prepared using the Chichibabin reactionof 4-aminopyridine (4-AP) and sodium amide indry dioxane, followed by alkylation with octyl iodide[25]. 4-OAP was isolated from the reaction mixture viaextraction with hexane and recrystallized first fromhexane and then from acetone (99.9%, m.p. 64 ±0.2C). The molecular and structural formulas wereconfirmed via elemental analysis plus IR and 1HNMR spectroscopy. OAP chloride was prepared byshaking a 0.1 M solution of 4-OAP (100 mL) with 1 MHCl (100 mL). The organic phase was separated andfiltered through a paper filter. All chloroform wasevaporated under an air stream. The residue was driedat 60C. The yield was 95%. According to the datafrom potentiometric titration, the content of the mainsubstance was 99.8%.Into 200L reactor was pumped n-octylamine 100kg, 30kg of 4-chloropyridine hydrochloride and 10kg of sodium fluoride were added, the temperature was raised to 130 C, and the mixture was stirred for 2 hours while keeping warm, Decompression recovery n-octylamine, while hot sodium carbonate aqueous solution to adjust the pH to about 7, adding ethyl acetate 120kg, separating the aqueous layer, the organic layer was cooled, filtered, Dried to give 4-octylaminopyridine 32.3kg, Purity was 99.3%, yield was 78.5%.

N-Octylpyridin-4-amine is used in the synthesis of antimicrobial agent Octenidine (O239150), as chelating agent.

Molecular Weight:206.33
XLogP3:4.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:8
Exact Mass:206.178298710
Monoisotopic Mass:206.178298710
Topological Polar Surface Area:24.9
Heavy Atom Count:15
Complexity:131
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes