3 alpha-high tropine aliphatic amine salt, crystal formation and preparation method

A technology of homotropane dihydrochloride and homotropane, which is applied in the field of six salts of 3α-homotropane and its crystal forms, and can solve the problem of 3α-homotropane that has not been seen. Amine Sulfate and other issues

Active Publication Date: 2009-06-03
SINOPHARM CHUANKANG PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no related reports on the sulfate, bisulfate, phosphate, dihydrogen diphosphate and tri-3α-homotropane diphosphate salts of 3α-homotropaneamine

Method used

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  • 3 alpha-high tropine aliphatic amine salt, crystal formation and preparation method
  • 3 alpha-high tropine aliphatic amine salt, crystal formation and preparation method
  • 3 alpha-high tropine aliphatic amine salt, crystal formation and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 10g of 3α-homotropaneamine and 30ml of methanol into a 250ml flask, stir, add 6ml of 12N hydrochloric acid dropwise, cool to room temperature and crystallize. Filtration gave 13.6 g of a white powdery solid product. Yield: 92.2%. In X-ray powder characteristic diffraction spectrum, the diffraction peaks 2θ are 9.90°, 11.648°, 14.643°, 16.118°, 17.748°, 19.568°, 19.956°, 21.765°, 24.950°, 29.407°, 29.789°, 31.198°, 32.345° °, 35.567°, the characteristic peaks in the infrared spectrum appear at 3294, 2868, 2089, 1655, 1613, 1519, 1408, 1322, 1214, 1154, 1038, 963, 693, 589, 503cm -1 place.

Embodiment 2

[0033] Add 15g of 3α-homotropane amine and 80ml of ethanol into a 500ml flask, stir, add 10ml of 12N hydrochloric acid dropwise, cool to room temperature and crystallize. After filtration, 20.2 g of a white powdery solid product was obtained, yield: 91.4%. In X-ray powder characteristic diffraction spectrum, the diffraction peaks 2θ are 9.90°, 11.648°, 14.643°, 16.118°, 17.748°, 19.568°, 19.956°, 21.765°, 24.950°, 29.407°, 29.789°, 31.198°, 32.345° °, 35.567°, the characteristic peaks in the infrared spectrum appear at 3294, 2868, 2089, 1655, 1613, 1519, 1408, 1322, 1214, 1154, 1038, 963, 693, 589, 503cm -1place.

[0034] (this method is the preferred version of the present invention)

Embodiment 3

[0036] Add 15g of 3α-homotropane amine and 100ml of ethanol into a 500ml flask, stir, add 9.5g of sulfuric acid dropwise, cool to room temperature and crystallize. After filtration, 20.3 g of a light red powdery solid product was obtained, yield: 82.8%. In X-ray powder characteristic diffraction spectrum, the diffraction peaks 2θ are 13.394°, 15.144°, 16.487°, 16.964°, 17.691°, 18.109°, 18.616°, 19.553°, 20.002°, 20.719°, 21.115°, 21.654°, 23.596 °, 24.320°, 24.832°, 25.399°, 25.882°, 28.008°, 30.079°, 30.560°, 31.106°, 33.380°, 33.864°, 35.511°, 36.771°, the characteristic peaks in the infrared spectrum appear at 3435, 2930, 1632 , 1535, 1508, 1484, 1456, 1370, 1121, 1035, 967, 619cm -1 place.

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Abstract

The invention relates to a 3 alpha-high tropine aliphatic amine salt, crystal formation and preparation method, which is to resolve problems of poor stability for preparing midbody of Granisetron, inconvenience for storage and transportation and low purity of final products. The 3 alpha-high tropine aliphatic amine is dissolved in one or more organic solvents and 1-10 equivalent hydrochloric acid, sulphuric acid or phosphoric acid are added in for crystallization and filtration after mixing to cool. 1 to 20-fold water and 10 to 100-fold alcohols solvent are used for recrystallization for cooling, crystallization, filtration and vacuum drying for 12 hours.

Description

Technical field: [0001] The invention relates to a 3α-homotropaneamine salt and its crystal form, in particular to six salts of 3α-homotropaneamine and its crystal forms, including its preparation method and recrystallization method. The crystal form 3α-homotropane amine salt is used for synthesizing granisetron hydrochloride, an antiemetic drug for chemotherapy. Background technique: [0002] The chemical name of 3α-homotropinamine is Endo-3-amine-9-methyl-9-azabicyclo[3,3,1]nonane-3-amine (Endo-9-methyl-9-azabicyclo[ 3.3.1] nonan-3-amine). It is an important intermediate in the synthesis of granisetron hydrochloride, a chemotherapy antiemetic drug. Related synthesis methods are reported in: WO96 / 03401, CN1190436C. Using 3α-homotropaneamine as an intermediate, its chemical properties are active, it is easy to turn yellow due to light after a long time, and it is easy to react with carbon dioxide in the air to form carbonate, which will affect the progress of the next rea...

Claims

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Application Information

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IPC IPC(8): C07D451/14
Inventor 艾林张乐刘啸卢铁刚王嘉勇
Owner SINOPHARM CHUANKANG PHARMACEUTICAL CO LTD
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