Octenidine dihydrochloride synthesis
- Product Name:Octenidine dihydrochloride
- CAS Number:70775-75-6
- Molecular formula:C36H64Cl2N4
- Molecular Weight:623.8262
Octenidine dihydrochloride is a cationic surfactant, with a gemini-surfactant structure, derived from pyridine. It is active against Gram-positive and Gram-negative bacteria. Octenidine dihydrochloride is synthesised by 1,10-Dichlorodecane and N-octylpyridin-4-amine.
2162-98-3
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64690-19-3
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70775-75-6
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$6.00/50mg
Yield:70775-75-6 85.1%
Reaction Conditions:
in acetic acid butyl ester for 12 h;Reflux;
Steps:
4 EXAMPLE 4: Preparation of octenidine dihydrochloride
159.7 g (0.774 mol) of A/-octylpyridin-4-amine obtained in example 3 were added to 240 ml of n-butyl acetate. The resulting suspension was heated to reflux temperature and 82.6 ml (0.387 mol) of 1 ,10-dichlorodecane were added dropwise. The reaction mixture was stirred for 12 hours at reflux temperature. After cooling to 40-50 °C, 966 ml of acetone and 241 ml of dimethylsulfoxide were added. The resulting suspension was heated to reflux temperature and water was added until complete dissolution. The solution was then cooled to 0-5°C and stirred at this temperature for 1 hour. After collecting by filtration the precipitated solid, 308 ml of acetone and then 53 ml of water were added. The resulting suspension was heated to reflux temperature and the solution obtained was filtered. Afterwards, 1129 ml of acetone were added onto the filtrate. After heating the resulting suspension to reflux temperature, water was added until complete dissolution. The solution was then cooled to 0-5°C and stirred at this temperature for 1 hour. The resulting suspension was filtered, obtaining a white solid which was dried at 45-50 °C under vacuum to give 201.2 g of octenidine dihydrochloride (Total yield: 85.1 % based on A/-octylpyridin-4-amine). Purity (% area, HPLC): 99.91 %. XRPD: Diffraction peaks at (2Q, degrees): 2.5, 4.9, 18.3, 19.6, 20.1 , 23.5, 26.9 and 27.1 ± 0.2 (See Figure 2).
References:
MEDICHEM, S.A. WO2021/13997, 2021, A1 Location in patent:Page/Page column 13-14
504-24-5
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70775-75-6
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$6.00/50mg
124-13-0
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70775-75-6
263 suppliers
$6.00/50mg