JPS59206352A - Production of 2-methoxy-5-sulfamoylbenzoyl-(n-ethyl)-2- pyrrolidinemethylamine - Google Patents
Production of 2-methoxy-5-sulfamoylbenzoyl-(n-ethyl)-2- pyrrolidinemethylamineInfo
- Publication number
- JPS59206352A JPS59206352A JP8151483A JP8151483A JPS59206352A JP S59206352 A JPS59206352 A JP S59206352A JP 8151483 A JP8151483 A JP 8151483A JP 8151483 A JP8151483 A JP 8151483A JP S59206352 A JPS59206352 A JP S59206352A
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- methoxy
- formula
- pyrrolidinemethylamine
- sulfamoylbenzoyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Pyrrole Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は医薬品として有用な２−メトキシ−５−スルフ
ァモイルベンゾイル−（Ｎ−エチル）−２−ピロリジン
メチルアミンの製造方法に関するものであり、その製法
は ２−メトキシ−５−スルファモイル安息香酸とｌ−
エチル−２−アミノメチルピロリジンを適当な条件下に
触媒を用い直接反応させ２−メトキシ−５−スルフ７モ
イルベンノイルー（Ｎ−エチル）−２−ピロリジンメチ
ルアミンを製造する事にある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 2-methoxy-5-sulfamoylbenzoyl-(N-ethyl)-2-pyrrolidinemethylamine, which is useful as a pharmaceutical. -5-sulfamoylbenzoic acid and l-
The purpose of the present invention is to directly react ethyl-2-aminomethylpyrrolidine using a catalyst under appropriate conditions to produce 2-methoxy-5-sulf7moylbennoyl(N-ethyl)-2-pyrrolidinemethylamine.
従来の文献並びに特許では水晶の製法について数多くの
方法が発表されている。即ち、 安息香酸誘導体を反応
性に富んだ官能基５例えば、酸ハライド、エステル等に
置きかえてアミン類と反応させる方法。In conventional literature and patents, many methods for manufacturing crystals have been published. That is, a method in which a benzoic acid derivative is replaced with a highly reactive functional group 5, such as an acid halide, an ester, etc., and reacted with an amine.
ルイス酸、リン化合物その他の触媒を用いて安息香酸誘
導体とアミン類を直接反応させる方法、ｊ高沸点ｉ＠媒
或は脱水剤を用いて両者を直接反応させる方法等が数多
く報告されている。Many methods have been reported, including a method in which benzoic acid derivatives and amines are directly reacted using a Lewis acid, a phosphorus compound, or other catalyst, and a method in which the two are directly reacted using a high-boiling point i@@ medium or a dehydrating agent.
しかし、これらの方法は操・作が繁雑であるか、高温或
は長時間を要し。However, these methods are complicated to operate, require high temperatures, or require a long time.
収率が低い等の欠点を有している。It has drawbacks such as low yield.
本発明はこれらの欠点を克服すべく鋭意研究を重ねた結
果、繁雑な中間体の合成経路を経ることなく直接、安息
香酸とアミンの両誘導体を適当な反応条件下に触媒を用
いて一挙に且つ高収率で工業的に、しかも経済的に水晶
を製造する方法に到達した。As a result of intensive research aimed at overcoming these drawbacks, the present invention has been developed to directly synthesize both benzoic acid and amine derivatives at once using a catalyst under appropriate reaction conditions without going through a complicated intermediate synthesis route. In addition, we have achieved a method for producing crystals industrially and economically with high yield.
その反応式を図示すれば次の通りである。The reaction formula is illustrated as follows.
即ち、２−メトキシ−５−ヌルフッモイル安息香酸（Ｉ
Ｉに１−エチル−２−７ミノメチルビロリジン（Ｉ［）
を加え攪拌しつ工、Ｉ、＞メｆルホルムアミドにシアノ
リン酸ジエチルｍ＋を溶解した液を滴下し、目的物（Ｖ
ｉｌを容易に製造する。本方法は安息香酸とアミンの両
誘導体を容易に入手若しくは製造し得るシアノリン酸ジ
エチルを触媒として室温で短時間に極めて有利な条件下
に且、高収率で水晶を製造し得るものである。That is, 2-methoxy-5-nurfumoylbenzoic acid (I
I is 1-ethyl-2-7minomethylpyrrolidine (I[)
A solution of diethyl cyanophosphate m+ dissolved in methylformamide was added dropwise to obtain the desired product (V
il is easily produced. This method uses diethyl cyanophosphate, from which both benzoic acid and amine derivatives can be easily obtained or produced, as a catalyst, and can produce crystals at room temperature in a short time under extremely advantageous conditions and in high yield.
以下実施例を挙（すて本発明の詳細な説明する。The present invention will be described in detail below by way of examples.
（実施例）
Ｉｏｏ鉱のジメチルホルムアミドに２３．１ Ｆ （０
，１モル）の２−メトキシ−５−スルファモイル安息香
酸と１２．４Ｆ（０，１モル）１−工ｆルー２−７ミノ
メテルビロ：ノジｌとを加北攪拌する。(Example) 23.1 F (0
, 1 mol) of 2-methoxy-5-sulfamoylbenzoic acid and 12.4F (0.1 mol) 1-method-2-7 minometerbilo:nojil were stirred together.
別にジメチルホルムアミドにシアノリン酸ジエｆ）Ｖ２
Ｏり（０１３モル）を溶解した液を反応液に滴下する。Separately, diethyl cyanophosphate in dimethylformamide f) V2
A solution containing O2 (013 mol) is added dropwise to the reaction solution.
室温で、３時間攪拌し反応終了後、水中に分散し飽和炭
酸ナト９クム水溶液で結晶を洗滌する。After stirring for 3 hours at room temperature and after the reaction was completed, the crystals were dispersed in water and washed with a saturated aqueous solution of 9 cum of sodium carbonate.
融点 １７９〜１８０℃の２−メトキシ−５−スルフ７
モイルベンゾイルー（Ｎ−エチＪｖ）２−とロリジンメ
チルアミンの純品３２７２が得られｔ 収率９７チであ
る。2-Methoxy-5-sulfur 7 with melting point 179-180°C
A pure product of moylbenzoyl(N-ethyl Jv) 2- and loridine methylamine (3272) was obtained with a yield of 97.
手続補正書
特許庁長官 若 杉 和 夫 殿ｌ 事件ｑ１表
示 特許 ５８−０８１５１４２ 発 明の名称
２−メトキン−５−スルファモイルベンゾイル−（Ｎ−
エチル）−２−ピロリジンメチルアミンの製造方法
３ 補正をする者
４ 補正命令の日付 昭和５８年８月３０日５ 補正
の対象 発明の名称、特許請求の範囲１発明の詳細な
説明。Procedural Amendment Commissioner of the Patent Office Kazuo Wakasugi Case Q1 Display Patent 58-0815142 Title of Invention
2-methquin-5-sulfamoylbenzoyl-(N-
Process for producing (ethyl)-2-pyrrolidine methylamine 3 Person making the amendment 4 Date of amendment order August 30, 1980 5 Subject of amendment Title of the invention, scope of claims 1 Detailed description of the invention.
逼に邊挿粕も１話There is also 1 episode of Takuya
Claims (1)
ル−２−アミノメチルピロリジンなりアノリン酸ジエチ
ルの存在下に直接反応させることを特徴とする２−メト
キン−５−スルファモイルベンゾイル−（Ｎ−エチル）
−２−ピロリジンメチルアミンの製造方法。2-methoxy-5-sulfamoylbenzoyl-(N-ethyl )
-A method for producing 2-pyrrolidinemethylamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8151483A JPS59206352A (en) | 1983-05-10 | 1983-05-10 | Production of 2-methoxy-5-sulfamoylbenzoyl-(n-ethyl)-2- pyrrolidinemethylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8151483A JPS59206352A (en) | 1983-05-10 | 1983-05-10 | Production of 2-methoxy-5-sulfamoylbenzoyl-(n-ethyl)-2- pyrrolidinemethylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS59206352A true JPS59206352A (en) | 1984-11-22 |
Family
ID=13748450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8151483A Pending JPS59206352A (en) | 1983-05-10 | 1983-05-10 | Production of 2-methoxy-5-sulfamoylbenzoyl-(n-ethyl)-2- pyrrolidinemethylamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59206352A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804265A (en) * | 2012-11-08 | 2014-05-21 | 江苏天士力帝益药业有限公司 | Synthesis and post-processing method of sulpiride or optical isomer thereof |
-
1983
- 1983-05-10 JP JP8151483A patent/JPS59206352A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804265A (en) * | 2012-11-08 | 2014-05-21 | 江苏天士力帝益药业有限公司 | Synthesis and post-processing method of sulpiride or optical isomer thereof |
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