JPS5849550B2 - Synchronous aniline usage information - Google Patents
Synchronous aniline usage informationInfo
- Publication number
- JPS5849550B2 JPS5849550B2 JP49016062A JP1606274A JPS5849550B2 JP S5849550 B2 JPS5849550 B2 JP S5849550B2 JP 49016062 A JP49016062 A JP 49016062A JP 1606274 A JP1606274 A JP 1606274A JP S5849550 B2 JPS5849550 B2 JP S5849550B2
- Authority
- JP
- Japan
- Prior art keywords
- melting point
- group
- acid
- methoxyphenyl
- aniline
- 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.)
- Expired
Links
Landscapes
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は一般式（Ｉ）
〔式中、Ｒ１は低級アルキル基、低級アルコキシル基ま
たはハロゲン原子を、Ａは
（式中、
Ｒ２は低級ア
ルキル基、低級アルコキシル基またはハロゲン原子を意
味する。Detailed Description of the Invention The present invention relates to the general formula (I) [wherein R1 is a lower alkyl group, a lower alkoxyl group, or a halogen atom, and A is (in the formula, R2 is a lower alkyl group, a lower alkoxyl group, or a halogen atom] means an atom.
）を、およびｎは１から３までの整数を意味する。), and n means an integer from 1 to 3.
〕で表わされる新規なアニリン誘導体の製法に関する。] This invention relates to a method for producing a novel aniline derivative represented by:
前記一般式〔０において、低級アルキル基としては、メ
チル基、エチル基、ｎ−プロビル基、ｉｓｏフ゛０ピ′
基） ｎ−フ゛チノレ基、 Ｓｅｅ−フ゛チノレ基、ｉ
ｓｏ−ブチル基、ｔｅｒ−ブチル基、ｎ−ベンチル基、
ｎ−ヘキシル基、ｎ−ヘプチル基などを、低級アルコキ
シル基としては、メトキン基、エトキシ基、ｎ−プロポ
キシ基、ｉｓｏ−プロポキシ基、ｎ−ブトキシ基、ｉｓ
ｏ−ブトキシ基、Ｓｅｅ−ブトキシ基、ｎ−ペントキシ
基、ｎ−へキシルオキシ基、ｎ−へプチルオキシ基など
を、ハロゲン原子としてはフッ素、塩素、臭素またはヨ
ウ素原子を表わす。In the general formula [0], the lower alkyl group includes methyl group, ethyl group, n-propyl group,
group) n-butylene group, See-phytyl group, i
so-butyl group, ter-butyl group, n-bentyl group,
n-hexyl group, n-heptyl group, etc., lower alkoxyl group includes methquine group, ethoxy group, n-propoxy group, iso-propoxy group, n-butoxy group, is
An o-butoxy group, a See-butoxy group, an n-pentoxy group, an n-hexyloxy group, an n-heptyloxy group, etc. are represented, and the halogen atom is a fluorine, chlorine, bromine or iodine atom.
本発明の方法は一般式■ 〔式中、Ｒ１、Ａおよびｎは前記と同じ意味を表わす。The method of the present invention is based on the general formula ■ [In the formula, R1, A and n represent the same meanings as above.
〕≦で表わされる化合物を還元し、かつ必要に応じて酸
塩することを特徴とする前記一般式〔■〕で表わされる
新規なアニリン誘導体およびその酸塩の製法である。] This is a method for producing a novel aniline derivative represented by the general formula [■] and its acid salt, which is characterized by reducing the compound represented by ≦ and converting it into an acid acid salt if necessary.
本発明の反応は、水素化金属化合物、たとえば水素化ア
ルミニウム化合物、水素化ホウ素化合物などの還元剤と
適当な溶媒たとえばジエチルエーテル、ｎ−ジブチルエ
ーテル、テトラヒドロフラン、シオキサン、メチラール
、Ｎ一エチルモルホリンなどの溶媒中、室温または加熱
して行なう。The reaction of the present invention is carried out using a reducing agent such as a metal hydride compound, such as an aluminum hydride compound or a borohydride compound, and a suitable solvent such as diethyl ether, n-dibutyl ether, tetrahydrofuran, thioxane, methylal, N-ethylmorpholine, etc. It is carried out in a solvent at room temperature or with heating.
還元剤としてはたとえば水素化アルミニウム化合物、特
に水素化リチウムアルミニウムが好適である。Suitable reducing agents are, for example, aluminum hydride compounds, especially lithium aluminum hydride.
本発明の出発原料である一般弐四の化合物は、通常の方
法により容易に製造され得るが、一例を挙げるならば次
のごとくである。The general 24 compounds which are the starting materials of the present invention can be easily produced by conventional methods, and one example is as follows.
〔式中、Ｒ１、Ａおよびｎは前記と同じ意味を有し、Ｘ
はハロゲン原子を表わす。[In the formula, R1, A and n have the same meanings as above, and
represents a halogen atom.
〕前記一般式〔０で表わされる新規なアニリン誘導体は
無機酸または有機酸、たとえば塩酸、硫酸、硝酸、燐酸
、ギ酸、酢酸、シュウ酸、マロン酸、コハク酸、乳酸、
リンゴ酸、酒石酸、クエン酸、マレイン酸、フマール酸
、サリチル酸、ｐ一トルエンスルホン酸などと酸付加塩
を形成する。] The novel aniline derivative represented by the general formula [0] is an inorganic or organic acid, such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, oxalic acid, malonic acid, succinic acid, lactic acid,
Forms acid addition salts with malic acid, tartaric acid, citric acid, maleic acid, fumaric acid, salicylic acid, p-toluenesulfonic acid, etc.
本発明方法により得られる新規アニリン誘導体は中枢神
経作用を有し、医薬品として重要なものである。The novel aniline derivatives obtained by the method of the present invention have central nervous system effects and are important as pharmaceuticals.
次に実施例をあげて本発明の方法をさらに詳し《説明す
るが、イ司らこれのみにとらわれるものでないことはい
うまでもない。Next, the method of the present invention will be explained in more detail with reference to Examples, but it goes without saying that the present invention is not limited to these examples.
実施例
水素化リチウムアルミニウム０．９５Ｐ、テトラヒドロ
フラン２０ｍｌ！の混合物に冷却しながら、ｐフルオル
ー３−（４−（ｏ−メトキシフエニル）１−ピペラジニ
ル〕プロピオンアニリド４．４５１、テトラヒドロフラ
ン３０ｒｒＬｌの溶液を滴下し、その後還流下で３時間
加熱した。Example Lithium aluminum hydride 0.95P, tetrahydrofuran 20ml! A solution of 4.451 l of p-fluoro-3-(4-(o-methoxyphenyl)1-piperazinyl)propionanilide and 30 rrL of tetrahydrofuran was added dropwise to the mixture while cooling, and then heated under reflux for 3 hours.
再び冷却し水分解、そしてベンゼンを加えて攪拌したの
ち有機層を分離した。After cooling again to decompose water, benzene was added and stirred, the organic layer was separated.
有機層は乾燥後減圧で溶媒を留去すると融点７９〜８０
℃の１−（３−（ｐ−フルオルアニリノ）フロピル’）
−４−（ｏ−メトキシフエニル）ピペラジンが得られた
。The organic layer has a melting point of 79-80 when the solvent is distilled off under reduced pressure after drying.
1-(3-(p-fluoroanilino)furopyl') at °C
-4-(o-methoxyphenyl)piperazine was obtained.
シクロヘキサンから再結晶すると融点８４〜８４．５℃
を与えた。Melting point: 84-84.5℃ when recrystallized from cyclohexane
gave.
同様にして次の化合物を得た。The following compound was obtained in the same manner.
■−〔３−（ｐ−フルオルアニリノ）プロビル〕４−（
ｏ一エトキシフエニル）ヒペラシン、融点１０１〜１０
１．５℃。■-[3-(p-fluoroanilino)provil]4-(
o-ethoxyphenyl) hyperacin, melting point 101-10
1.5℃.
１−（３−（ｐ−フルオルアニリノ）フロピル〕４−（
０−ｎ−プロポキシフエニル）ピペラジン、融点７６〜
７７℃。1-(3-(p-fluoroanilino)furopyl)4-(
0-n-propoxyphenyl)piperazine, melting point 76~
77℃.
１−（３−（ｐ−フルオルアニリノ）プロピル４−（Ｏ
−ｉｓＯ−プロポキシフエニル）ピペラジン、融点７９
〜８０℃。1-(3-(p-fluoroanilino)propyl 4-(O
-isO-propoxyphenyl)piperazine, melting point 79
~80℃.
１−〔３−（ｐ一トルイジノ）プロビル〕−４（０−メ
トキシフエニル）ピペラジン、融点７２〜７３℃。1-[3-(p-toluidino)probyl]-4(0-methoxyphenyl)piperazine, melting point 72-73°C.
１−（ ３−（ｐ一エチルアニリノ）一プロピル〕４−
（ｏ一エトキシフエニル）ヒペラジンシュウ酸塩、融点
１１５〜１１６℃（分解）
１−〔３−（ｐ−アニシジノ）プロビル〕−４−（０−
メトキシフエニル）ピペラジン、融点８２〜８２．５℃
。1-(3-(p-ethylanilino)-propyl)4-
(o-ethoxyphenyl)hyperazine oxalate, melting point 115-116°C (decomposition) 1-[3-(p-anisidino)probyl]-4-(0-
methoxyphenyl)piperazine, melting point 82-82.5°C
.
１−（３−（ｐ−フルオルアニリノ）プロビル〕４−（
ｏ−クロルフエニル）ヒペラジン塩酸塩、融点２４０℃
以上。1-(3-(p-fluoroanilino)probyl)4-(
o-chlorophenyl)hiperazine hydrochloride, melting point 240°C
that's all.
１ − （ ３−（ ｐ−フルオルアニリノ）フロビル
〕４−（ｏ一トリル）ピペラジン塩酸塩、融点２４０℃
以上。1-(3-(p-fluoroanilino)furovir)4-(o-montolyl)piperazine hydrochloride, melting point 240°C
that's all.
１−〔３−（ｐ−クロルアニリノ）フロピル〕４ −
（ ｏ一エトキシフエニル）ヒペラジン、融点９０〜９
１℃。1-[3-(p-chloroanilino)furopyl]4-
(o-ethoxyphenyl)hyperazine, melting point 90-9
1℃.
１−〔２−（ｐ−フルオルアニリノ）エチル〕４−（ｏ
−メトキシフエニル）ピペラジン塩酸塩、融点１９９〜
２００℃（分解）
１−（４−（ｐ−フルオルアニリノ）フチル〕４−（Ｏ
−メトキシフエニル）ピペラシンシュウ酸塩、融点１０
０〜１ ０ １ ’Ｃ （分解）１−〔３−（ｍ−フル
オルアニリノ）プロビル〕４−（ｏ−メトキシフエニル
）ピペラジン塩酸塩、融点２２７〜２２８℃（分解）
１−〔３−（ｏ−フルオルアニリノ）フロビル〕４−（
Ｏ−メトキシフエニル）ピペラシンシュウ酸塩、融点１
４８〜１４８．５℃（分解）なお原料化合物は次のよう
にして製造した。1-[2-(p-fluoroanilino)ethyl]4-(o
-methoxyphenyl)piperazine hydrochloride, melting point 199~
200℃ (decomposition) 1-(4-(p-fluoroanilino)phthyl]4-(O
-methoxyphenyl)piperacin oxalate, melting point 10
0-1 0 1 'C (decomposition) 1-[3-(m-fluoroanilino)probyl]4-(o-methoxyphenyl)piperazine hydrochloride, melting point 227-228°C (decomposition) 1-[3-(o -fluoroanilino)furovir]4-(
O-methoxyphenyl)piperacine oxalate, melting point 1
48-148.5°C (decomposition) The raw material compound was produced as follows.
参考例
３−クロルーｐ−フルオルプロピオンアニリト６ｆ、１
−（ｏ−メトキシフエニル）ピペラジン５．８１、炭酸
ナトリウム１．６１、ジメチルホルムアミド１２０ｒｒ
Ｌｌの混合物を８０〜９０℃で２５時間攪拌下、加熱し
た。Reference Example 3-Chloro-p-fluoropropionanilide 6f, 1
-(o-methoxyphenyl)piperazine 5.81, sodium carbonate 1.61, dimethylformamide 120rr
The mixture of Ll was heated at 80-90°C for 25 hours with stirring.
放冷後、反応混合物を水の中に注入し、分離する油状物
をベンゼンで抽出した。After cooling, the reaction mixture was poured into water, and the oil that separated was extracted with benzene.
有機層は無水芒硝で乾燥後、減圧で溶媒を留去した。The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
得られた油状物をエーテルで結晶化させるとｐ−フルオ
ルー３−（４−（ｏ−メトキシフエニル）−１−ピペラ
ジニル〕フロヒオンアニリトが得られた。The resulting oil was crystallized from ether to yield p-fluor-3-(4-(o-methoxyphenyl)-1-piperazinyl)flohionanilite.
融点１１８〜１２０℃。Melting point 118-120°C.
シクロヘキサンから再結晶すると融点１２５〜１２６℃
を与えた。Melting point: 125-126℃ when recrystallized from cyclohexane
gave.
同様にして次の化合物を得た。The following compound was obtained in the same manner.
ｐ−フルオル−３−〔４−（ｏ一エトキシフエニル）−
１−ピペラジニル〕フロピオンアニリト融点 １００
〜１０Ｆｃ
ｐ−フルオルー３−〔４−（ｏ−ｎ−グロポキシフエニ
ル）−１−ピペラジニル〕フロピオンアニリド
融点 ９０〜９ １ ’Ｃ
ｐ−フルオル−３−（４−（ｏ−ｉｓｏ−７ロポキシフ
エニル）−１−ピペラジニル〕グロピオンアニリド
融点 ９０〜９０．５℃
３−〔４−（ｏ−メトキシフエニル）−１−ピペラジニ
ル〕フロピオンーｐ−トルイシト融点 １２４〜１２４
．５℃
ｐ一エチル−３−〔４−（ｏ一エトキシフエニル）−１
−ピペラジニル〕フロピオンアニリト融点 １１０〜
１’ｌｌ’Ｃ
３−〔４−（ｏ−メトキシフエニル）−１−ピヘラシニ
ル〕フロピオンーｐ−７ニシシト融点 １５２〜１５
３℃
ｐ−フルオル−３−〔４−（ｏ−クロルフエニル）−１
−ピペラジニル〕フロヒオンアニリト融点 １１５．５
〜１１６℃
ｐ−フルオルー３−〔４−（ｏ一トリル）−１ピペラジ
ニル〕プロピオンアニリド
融点 １２５〜１２６℃
ｐ−クロルー３−〔４−（ｏ一エトキシフエニル） −
１−ヒペラジニル〕フロピオンアニリド融点 １１５〜
１１５．５゜Ｃ
ｐ−フルオルー２−（４−（ｏ−メトキシフエニル）−
１−ピペラジニル〕アセトアニリド融点 １３２〜１
３４゜Ｃ
ｐ−フルオルー４−（４−（ｏ−メトキシフエニル）−
１−ピペラジニル〕プチロアニリドその塩酸塩の融点
２１１〜２１２℃（分解）ｍ−フルオルー３−（４−（
ｏ−メトキシフエニル）−１−ピペラジニル〕フロピオ
ンアニリト融点 １１２〜３℃p-Fluoro-3-[4-(o-ethoxyphenyl)-
1-piperazinyl]fropionanilite Melting point 100
~10Fc p-fluoro-3-[4-(on-glopoxyphenyl)-1-piperazinyl]fropionanilide Melting point 90-9 1'C p-fluoro-3-(4-(o-iso-7 3-[4-(o-methoxyphenyl)-1-piperazinyl]propion-p-toluicite melting point 124-124
．． 5℃ p-ethyl-3-[4-(o-ethoxyphenyl)-1
-Piperazinyl]fropionanilide Melting point 110~
1'll'C 3-[4-(o-methoxyphenyl)-1-pyheracinyl]flopion-p-7 Nishishito Melting point 152-15
3°C p-fluoro-3-[4-(o-chlorophenyl)-1
-piperazinyl]flohionanilide Melting point 115.5
~116°C p-fluoro-3-[4-(o-tolyl)-1piperazinyl]propionanilide Melting point 125-126°C p-chloro-3-[4-(o-ethoxyphenyl)-
1-hyperazinyl]fropionanilide Melting point 115~
115.5°C p-fluoro-2-(4-(o-methoxyphenyl)-
1-Piperazinyl]acetanilide Melting point 132-1
34°C p-Fluor-4-(4-(o-methoxyphenyl)-
Melting point of 1-piperazinyl]butyloanilide its hydrochloride
211-212℃ (decomposition) m-fluoro-3-(4-(
o-methoxyphenyl)-1-piperazinyl] fropionanilide Melting point 112-3°C
Claims (1)
たはハロゲン原子を、Ａは （式中、 Ｒ２は低級ア ルキ基、低級アルコキシル基またはハロゲン原子を意味
する。 ）を意味し、およびｎは１から３までの整数を意味する
。 〕で表もされる化合物を還元し、かつ必要に応じて酸塩
とすることを特徴とする一般式 （式中、Ｒ１、Ａおよびｎは前記と同じ意味を有する。 ）で表わされる新規なアニリン誘導体の製法。[Scope of Claims] 1 General formula [In the formula, R1 represents a lower alkyl group, a lower alkoxyl group, or a halogen atom, and A represents (In the formula, R2 represents a lower alkyl group, a lower alkoxyl group, or a halogen atom.) and n means an integer from 1 to 3. ] A novel compound represented by the general formula (wherein R1, A and n have the same meanings as above), which is characterized by reducing the compound represented by Method for producing aniline derivatives.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49016062A JPS5849550B2 (en) | 1974-02-07 | 1974-02-07 | Synchronous aniline usage information |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49016062A JPS5849550B2 (en) | 1974-02-07 | 1974-02-07 | Synchronous aniline usage information |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50108264A JPS50108264A (en) | 1975-08-26 |
| JPS5849550B2 true JPS5849550B2 (en) | 1983-11-05 |
Family
ID=11906077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49016062A Expired JPS5849550B2 (en) | 1974-02-07 | 1974-02-07 | Synchronous aniline usage information |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5849550B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59230441A (en) * | 1983-06-08 | 1984-12-25 | Mitsubishi Electric Corp | Field unit of rotary electric machine |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8303946D0 (en) * | 1983-02-12 | 1983-03-16 | Recordati Chem Pharm | Antihypertensive n-piperazinylalkanoylanilides |
| DE4319039A1 (en) * | 1993-06-08 | 1994-12-15 | Bayer Ag | Substituted (2-oxo-1-benzimidazolinyl) -piperidines, process for their preparation and use as anti-retroviral agents |
| CA2341542A1 (en) * | 1999-06-24 | 2000-12-28 | Toray Industries, Inc. | .alpha.1b-adrenergic receptor antagonists |
| SE9904738D0 (en) * | 1999-12-22 | 1999-12-22 | Astra Pharma Prod | Novel compounds |
| CA2503720A1 (en) * | 2002-10-30 | 2004-05-21 | Merck & Co., Inc. | Gamma-aminoamide modulators of chemokine receptor activity |
| DE102005038141A1 (en) * | 2005-08-12 | 2007-02-15 | Grünenthal GmbH | Substituted 8- (3-aminopropyl) -1-phenyl-1,3,8-triaza-spiro [4.5] decan-4-one derivatives |
| CN113620863B (en) * | 2015-09-14 | 2024-04-05 | 内盖夫国家生物技术研究所 | Piperazine and piperidine derivatives, their synthesis and use |
| US10434099B2 (en) | 2016-09-22 | 2019-10-08 | The National Institute for Biotechnology in the Negev Ltd. | Methods for treating central nervous system disorders using VDAC inhibitors |
| US10787423B2 (en) | 2015-09-14 | 2020-09-29 | The National Institute For Biotechnolgy In The Negev Ltd. | Piperazine and piperidine derivatives, their synthesis and use thereof in inhibiting VDAC oligomerization, apoptosis and mitochondria dysfunction |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3290317A (en) * | 1960-03-07 | 1966-12-06 | Sterling Drug Inc | 1-(nu-aryl-nu-alkanoylaminoalkyl)-4-aryl-4-piperidinols and their esters |
| US3350403A (en) * | 1964-04-07 | 1967-10-31 | Aldrich Chem Co Inc | Nu-phenyl amides of 4-phenyl-4-hydroxypiperidino alkyl acids |
| US3455935A (en) * | 1967-06-12 | 1969-07-15 | Miles Lab | 4-hydroxy-4-phenylpiperidines |
| US3539580A (en) * | 1967-06-26 | 1970-11-10 | Janssen Pharm | 4-aryl-4-aminoalkoxy-piperidines |
-
1974
- 1974-02-07 JP JP49016062A patent/JPS5849550B2/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3290317A (en) * | 1960-03-07 | 1966-12-06 | Sterling Drug Inc | 1-(nu-aryl-nu-alkanoylaminoalkyl)-4-aryl-4-piperidinols and their esters |
| US3350403A (en) * | 1964-04-07 | 1967-10-31 | Aldrich Chem Co Inc | Nu-phenyl amides of 4-phenyl-4-hydroxypiperidino alkyl acids |
| US3455935A (en) * | 1967-06-12 | 1969-07-15 | Miles Lab | 4-hydroxy-4-phenylpiperidines |
| US3539580A (en) * | 1967-06-26 | 1970-11-10 | Janssen Pharm | 4-aryl-4-aminoalkoxy-piperidines |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59230441A (en) * | 1983-06-08 | 1984-12-25 | Mitsubishi Electric Corp | Field unit of rotary electric machine |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50108264A (en) | 1975-08-26 |
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