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A technology of cinacalcet hydrochloride and reaction solvent, which is applied in the field of pharmaceutical preparation, can solve problems such as easy decomposition and instability, and achieve the effects of improving reaction selectivity, reducing pollution and reducing cost
Inactive Publication Date: 2013-12-25
NANJING LIFENERGY R & D
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2007, Volume 27, Issue 1, 1-7] also pointed out that sodium triacetoxyborohydride is used in the reductive amination reaction of various aldehydes and ketones with different amines, and is generally used in aprotic solvents, such as CH 2 Cl 2 , THF and acetonitrile, etc., but unstable in alcohol and water, easy to decompose
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Embodiment 1
[0031] Reaction system N 2 Protection, add tetrahydrofuran 280ml, R‐1‐(1‐naphthyl)ethylamine 11.8g and 3‐(trifluoromethyl)phenylpropanal 12.7g, stir at room temperature, add triacetoxy sodium borohydride 23g, acetic acid 14ml, stirred at room temperature for 24h, added 280ml10%Na 2 CO 3 Stirring, standing, separation, and HPLC test for purity, cinacalcet base 77.31%, R‐1‐(1‐naphthyl)ethylamine 10.13%, other impurities 12.56%, yield 84.5%.
Embodiment 2
[0033] Reaction system N 2 Protection, add tetrahydrofuran 280ml, purified water 20ml, R‐1‐(1‐naphthyl)ethylamine 11.8g and 3‐(trifluoromethyl)phenylpropanal 12.7g, stir at room temperature, add triacetoxy borohydrogenation Sodium 23g, acetic acid 14ml, stir at room temperature for 24h, add 260ml10%Na 2 CO 3 The solution was stirred, allowed to stand, separated, and tested for purity by HPLC. Cinacalcet base was 83.87%, R‐1‐(1‐naphthyl)ethylamine was 10.21%, other impurities were 5.92%, and the yield was 88.1%.
Embodiment 3
[0035] Reaction system N 2 Protection, add acetone 360ml, purified water 20ml, R‐1‐(1‐naphthyl)ethylamine 13.9g and 3‐(trifluoromethyl)phenylpropionaldehyde 12.7g, stir at room temperature, add triacetoxy borohydrogenation Sodium 38g, acetic acid 5ml, stir at room temperature for 12h, add 340ml of purified water and stir at 15‐20°C, let stand, separate liquid, and test purity by HPLC, cinacalcet base 93.24%, R‐1‐(1‐naphthyl ) Ethylamine 0.8%, other impurities 5.96%, yield 89.2%.
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Abstract
The present invention discloses a cinacalcet hydrochloride preparation method, which comprises: 1, adopting 3-(trifluoromethyl) phenyl propionaldehyde and R-1-(1-naphthyl)ethylamine as raw materials, and carrying out a condensation reduction reaction in a mixing reaction solvent in the presence of sodium triacetoxyborohydride, 2, extracting the reaction product with water, a salt or an alkali aqueous solution to obtain a cinacalcet base organic phase solution, and 3, carrying out acidification salification on the obtained cinacalcet base organic phase solution with hydrochloric acid to obtain the cinacalcet hydrochloride, wherein one of components in the mixing reaction solvent is water. According to the present invention, the water-containing mixing solvent is adopted as the reaction medium, such that technical defects of solvent use during the sodium triacetoxyborohydride use process are overcome, the harsh condition that the reaction solvent requires a water-free treatment is avoided while reaction selectivity is increased, types of produced impurities and impurity content are substantially reduced, cost is reduced, and environment pollution is reduced.
Description
technical field [0001] The invention belongs to the technical field of medicine preparation, and relates to a preparation method of cinacalcet hydrochloride. Background technique [0002] Cinacalcet hydrochloride is an internationally used N‐[(1R)‐1‐(1‐naphthyl)ethyl]‐3‐[3‐(trifluoromethyl)phenyl]propan‐1‐amine hydrochloride name, the compound CAS number is 364782-34-3, and the chemical formula is C 22 h 22 f 3 N HCl, the structural formula is as follows: [0003] [0004] Cinacalcet Hydrochloride (Cinacalcet Hydrochloride) is the first calcimimetic agent listed in the United States, Canada and Europe, which can significantly enhance the sensitivity of the calcium sensing receptors of parathyroid chief cells to extracellular calcium ions, and reduce parathyroid Glandular hormones and blood calcium, phosphorus concentration and calcium phosphorus product. It is known to be mainly used in the treatment of secondary hyperparathyroidism in patients with kidney disease on...
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