CN101987828B - 2-(N,N-dibenzylamino) methyl sulfone, and salt and application thereof - Google Patents
2-(N,N-dibenzylamino) methyl sulfone, and salt and application thereof Download PDFInfo
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- CN101987828B CN101987828B CN200910057693.7A CN200910057693A CN101987828B CN 101987828 B CN101987828 B CN 101987828B CN 200910057693 A CN200910057693 A CN 200910057693A CN 101987828 B CN101987828 B CN 101987828B
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- methyl sulfone
- salt
- amino
- ethyl
- dibenzylamino
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Abstract
The invention discloses 2-(amino) ethyl methyl sulfone hydrochloride which is an important intermediate for preparing antineoplastic medicaments. At present, in the conventional synthesis method, the 2-(amino) ethyl methyl sulfone is obtained by selectively reducing a sulfonyl group-containing cyano compound by diborane and by salification of the product and chlorine hydride. The cost is high when the diborane is used for reduction, so that the conventional method is not suitable for mass production. The invention provides a 2-(N,N-dibenzylamino) methyl sulfone and a salt thereof. The method for preparing the 2-(amino) ethyl methyl sulfone and the salt thereof from the 2-(N,N-dibenzylamino) methyl sulfone and the salt thereof is easy and convenient to operate and is suitable for industrial production.
Description
Technical field
The present invention relates to a kind of 2-(N, N-dibenzyl amino ethyl) methyl sulfone and salt thereof, prepare 2-(amino) ethyl-methyl sulfone and salt thereof for mass-producing.
Background technology
2-(amino) ethyl-methyl sulfone be synthetic some there is the important intermediate of antitumor activity composition.Bibliographical information 2-(amino) ethyl-methyl sulfone synthetic route is as follows:
Prepare hydrochloride.Preparation process large-scale industrial production operation difficulty, cost is high.
Summary of the invention
The shortcoming that 2-(amino) the ethyl-methyl sulfone hydrochloride of preparing for above route is difficult to large-scale production; the present invention relates to a kind of 2-(N; N-dibenzyl amino ethyl) methyl sulfone and salt thereof; through shortening, can prepare easily 2-(amino) ethyl-methyl sulfone and salt thereof by this compounds.2-(N, N-dibenzyl amino ethyl) methyl sulfone and salt structure thereof are as follows:
At the alkaline solution of the organic solvents such as alcohol, acid, ether, add 2-(N, N-dibenzyl amino ethyl) methyl sulfone or its salt, add Raney nickel or palladium carbon, hydro-reduction under certain pressure, obtains 2-(amino) ethyl-methyl sulfone or its salt.Reaction formula is as follows:
Thereby obtain respectively the different salt of 2-(amino) ethyl-methyl sulfone.
embodiment:
The preparation of 2-(amino) ethyl-methyl sulfone
In 1 liter of autoclave pressure, add 400 milliliters of ethanol, add 60 grams of 2-(N, N-dibenzyl amino ethyl) methyl sulfone, 15 grams of Raney nickel, logical hydrogen, to 20 kilograms of pressure, is heated to 50 degree, stirs reduction, and TCL follows the tracks of and reacts to raw material point hour.Cooling, releasing hydrogen gas, filters, concentrated, obtains 2-(amino) ethyl-methyl sulfone oily matter.
2-(amino) ethyl-methyl sulfone hydrochloride
2-obtained above (amino) ethyl-methyl sulfone is dissolved in to 100 milliliters of dehydrated alcohols, adds the ethanolic soln of hydrogenchloride, to pH2, stir 1 hour, filter filter cake washing with alcohol, dry, obtain 11 grams of 2-(amino) ethyl-methyl sulfone hydrochloride.
Claims (3)
1. 2-(N, N-dibenzyl amino) ethyl-methyl sulfone and salt thereof, structural formula is:
2. 2-as claimed in claim 1 (N, N-dibenzyl amino) ethyl-methyl sulfone and salt thereof are for the preparation of 2-(amino) ethyl-methyl sulfone and salt thereof.
3. the preparation method of a 2-(amino) ethyl-methyl sulfone and salt thereof, for by 2-(N claimed in claim 1, N-dibenzyl amino) ethyl-methyl sulfone and salt thereof makes through shortening, and the catalyzer using is Raney nickel, palladium carbon or platinum dioxide.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910057693.7A CN101987828B (en) | 2009-08-03 | 2009-08-03 | 2-(N,N-dibenzylamino) methyl sulfone, and salt and application thereof |
| EP09839039A EP2305634A1 (en) | 2009-05-12 | 2009-11-16 | The new preparation of aliphatic amines with sulphonyl group and their salts |
| PCT/CN2009/074958 WO2010130124A1 (en) | 2009-05-12 | 2009-11-16 | The new preparation of aliphatic amines with sulphonyl group and their salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910057693.7A CN101987828B (en) | 2009-08-03 | 2009-08-03 | 2-(N,N-dibenzylamino) methyl sulfone, and salt and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101987828A CN101987828A (en) | 2011-03-23 |
| CN101987828B true CN101987828B (en) | 2014-11-05 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200910057693.7A Expired - Fee Related CN101987828B (en) | 2009-05-12 | 2009-08-03 | 2-(N,N-dibenzylamino) methyl sulfone, and salt and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101987828B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002020365A (en) * | 2000-07-07 | 2002-01-23 | Sumitomo Seika Chem Co Ltd | Method for producing 2-(methylsulfonyl)ethylamine |
| EP1488809A1 (en) * | 2001-01-16 | 2004-12-22 | Glaxo Group Limited | Pharmaceutical combination containing a 4-quinazolineamine and another anti-neoplastic agent for the treatment of cancer |
| CN101367794A (en) * | 2007-07-20 | 2009-02-18 | 上海恒瑞医药有限公司 | Preparation method for quinazoline derivants and medical uses thereof |
-
2009
- 2009-08-03 CN CN200910057693.7A patent/CN101987828B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002020365A (en) * | 2000-07-07 | 2002-01-23 | Sumitomo Seika Chem Co Ltd | Method for producing 2-(methylsulfonyl)ethylamine |
| EP1488809A1 (en) * | 2001-01-16 | 2004-12-22 | Glaxo Group Limited | Pharmaceutical combination containing a 4-quinazolineamine and another anti-neoplastic agent for the treatment of cancer |
| CN101367794A (en) * | 2007-07-20 | 2009-02-18 | 上海恒瑞医药有限公司 | Preparation method for quinazoline derivants and medical uses thereof |
Non-Patent Citations (2)
| Title |
|---|
| 刘斯婕.拉帕替尼.《中国药物化学杂志》.2007,第17卷(第5期),第333页. * |
| 拉帕替尼;刘斯婕;《中国药物化学杂志》;20071031;第17卷(第5期);第333页 * |
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| Publication number | Publication date |
|---|---|
| CN101987828A (en) | 2011-03-23 |
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| PB01 | Publication | ||
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| C14 | Grant of patent or utility model | ||
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| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20141105 Termination date: 20210803 |