JPS6341907B2 - - Google Patents
Info
- Publication number
- JPS6341907B2 JPS6341907B2 JP9405578A JP9405578A JPS6341907B2 JP S6341907 B2 JPS6341907 B2 JP S6341907B2 JP 9405578 A JP9405578 A JP 9405578A JP 9405578 A JP9405578 A JP 9405578A JP S6341907 B2 JPS6341907 B2 JP S6341907B2
- Authority
- JP
- Japan
- Prior art keywords
- caprolactam
- amino
- chloroform
- mol
- allyl chloride
- 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
- -1 α-Substituted amino-ε-caprolactam Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 8
- BOWUOGIPSRVRSJ-UHFFFAOYSA-N 2-aminohexano-6-lactam Chemical compound NC1CCCCNC1=O BOWUOGIPSRVRSJ-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NDXGCVGKTPQXFA-UHFFFAOYSA-N 3-chloroazepan-2-one Chemical compound ClC1CCCCNC1=O NDXGCVGKTPQXFA-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- CFZGIDYCUWFUJR-UHFFFAOYSA-N 3-(dimethylamino)azepan-2-one Chemical compound CN(C)C1CCCCNC1=O CFZGIDYCUWFUJR-UHFFFAOYSA-N 0.000 description 1
- RITJPGRHUQHSST-UHFFFAOYSA-N 3-nitroazepan-2-one Chemical compound [O-][N+](=O)C1CCCCNC1=O RITJPGRHUQHSST-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- XXEWFEBMSGLYBY-SSDOTTSWSA-N n-dimethyl-lysine Chemical compound CN(C)CCCC[C@@H](N)C(O)=O XXEWFEBMSGLYBY-SSDOTTSWSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Description
本発明は一般式
（ここでR1は−CH2−CH＝CH2、R2は水素また
は−CH2−CH＝CH2を示す）
で表わされる新規なα−置換アミノ−ε−カプロ
ラクタムに関する。
本発明の化合物は、次式
もしくは
で示されるポリマーの原料またはアミン系エポキ
シ硬化促進剤として有用な物質である。
従来から知られているα−置換アミノ−ε−カ
プロラクタムとしてはアルキルまたはアラルキル
アミノ置換体がある。α−ジメチルアミノ−ε−
カプロラクタムはα−アミノ−ε−カプロラクタ
ムにホルマリンとパラジウムで処理して製造し、
N〓−ジメチルリジン金属塩合成の中間体として
報告されている（特公昭42−11926号公報）。また
α−クロル−ε−カプロラクタムとアルキルまた
はアラルキルアミンを反応させてα−アルキルま
たはα−アラルキルアミノ−ε−カプロラクタム
を製造し、殺菌剤としても報告されている（フラ
ンス特許第1441071号）。
本発明者らはα−アミノ−ε−カプロラクタム
に活性な官能基を導入することにより、更に有用
な物質を合成すべく鋭意研究を重ねた結果、本発
明に到達した。
即ち本発明のα−置換アミノ−ε−カプロラク
タムは前記一般式で表わされる化合物であるが、
具体的には次のような化合物である。
α−アリルアミノ−ε−カプロラクタム、α−
ジアリルアミノ−ε−カプロラクタムおよびこれ
らの塩。
本発明の化合物の製造方法は特に限定されるも
のではないが、例えば下式に示すごとくα−アミ
ノ−ε−カプロラクタムとアリルクロリドを反応
させることにより、得ることができる。
出発物質であるα−アミノ−ε−カプロラクタ
ムはα−クロル−ε−カプロラクタムのアミノ化
（特公昭46−23747号公報）、α−ニトロ−ε−カ
プロラクタムの還元（スイス国特許第375720号）、
α−アミノシクロヘキサノンオキシムのベツクマ
ン転位（特公昭41−18089号公報）、リジン低級ア
ルキルエステルの脱アルコール環化（特公昭46−
37352号公報）など種々の製造法が知られており、
これらいずれの方法で製造されたα−アミノ−ε
−カプロラクタムを使用しても良い。
反応温度は室温〜80℃で、反応温度によりアリ
ルクロライド１モル反応生成物、２モル反応生成
物を選択的に製造できる。すなわち低温条件では
アリルクロライド１モル反応生成物が、高温条件
では２モル反応生成物がそれぞれ選択的に多量に
製造できる。反応溶媒は水、アルコール類、クロ
ロホルム、四塩化炭素等のハロゲン化アルキル
類、ベンゼン、トルエン等のハイドロカーボン
類、エーテル類、又はアリルクロライド自身を溶
媒にすることができる。
以下実施例により本発明をさらに詳細に説明す
るが、本発明の化合物は特にこの製造法によつて
限定されるものではない。
実施例 １
特公昭41−18089号公報に示された方法により、
α−アミノシクロヘキサノンオキシム塩酸塩をベ
ツクマン転位して得たα−アミノ−ε−カプロラ
クタム12.8ｇ（0.1モル）をクロロホルム100mlに
とかし、撹拌装置、滴下ロート、還流管を装着し
た三口フラスコに仕込み、室温中にて撹拌した。
アリルクロライド3.8ｇ（0.05モル）をクロロホ
ルム50mlにとかし、ゆつくり室温中で滴下し、滴
下終了後、更に２時間反応させた。析出した結晶
をロ別し、クロロホルム層を水20mlで洗浄したの
ち、硫酸マグネシウムで脱水した。クロロホルム
を減圧で除去し濃縮した後蒸留し、bp119℃／0.1
mmHgの留分としてα−アリルアミノ−ε−カプ
ロラクタム7.5ｇを得た。収率74.3％、mp46〜７
℃。
The present invention is based on the general formula (Here, R 1 is -CH 2 -CH=CH 2 and R 2 is hydrogen or -CH 2 -CH=CH 2. ) The invention relates to a novel α-substituted amino-ε-caprolactam represented by: The compound of the present invention has the following formula: or It is a substance useful as a raw material for the polymer shown below or as an amine-based epoxy curing accelerator. Conventionally known α-substituted amino-ε-caprolactams include alkyl- or aralkylamino-substituted products. α-dimethylamino-ε-
Caprolactam is produced by treating α-amino-ε-caprolactam with formalin and palladium.
It has been reported as an intermediate in the synthesis of N-dimethyllysine metal salts (Japanese Patent Publication No. 11926/1983). It has also been reported that α-chloro-ε-caprolactam is reacted with an alkyl or aralkylamine to produce α-alkyl or α-aralkyl amino-ε-caprolactam as a fungicide (French Patent No. 1441071). The present inventors have conducted extensive research in order to synthesize a more useful substance by introducing an active functional group into α-amino-ε-caprolactam, and as a result, they have arrived at the present invention. That is, the α-substituted amino-ε-caprolactam of the present invention is a compound represented by the above general formula,
Specifically, the following compounds are used. α-allylamino-ε-caprolactam, α-
Diallylamino-ε-caprolactam and salts thereof. The method for producing the compound of the present invention is not particularly limited, but it can be obtained, for example, by reacting α-amino-ε-caprolactam with allyl chloride as shown in the following formula. The starting material α-amino-ε-caprolactam is obtained by amination of α-chloro-ε-caprolactam (Japanese Patent Publication No. 46-23747), reduction of α-nitro-ε-caprolactam (Swiss Patent No. 375720),
Beckman rearrangement of α-aminocyclohexanone oxime (Japanese Patent Publication No. 18089/1989), dealcoholization cyclization of lysine lower alkyl ester (Japanese Patent Publication No. 18089/1989),
Various manufacturing methods are known, such as (No. 37352),
α-Amino-ε produced by any of these methods
-Caprolactam may also be used. The reaction temperature is room temperature to 80°C, and a 1 mol allyl chloride reaction product or a 2 mol allyl chloride reaction product can be selectively produced depending on the reaction temperature. That is, a 1 mol reaction product of allyl chloride can be selectively produced in large quantities under low temperature conditions, and a 2 mol reaction product can be selectively produced under high temperature conditions. The reaction solvent can be water, alcohols, chloroform, alkyl halides such as carbon tetrachloride, hydrocarbons such as benzene and toluene, ethers, or allyl chloride itself. The present invention will be explained in more detail with reference to Examples below, but the compounds of the present invention are not particularly limited by this production method. Example 1 By the method shown in Japanese Patent Publication No. 41-18089,
12.8 g (0.1 mol) of α-amino-ε-caprolactam obtained by Beckman rearrangement of α-aminocyclohexanone oxime hydrochloride was dissolved in 100 ml of chloroform, charged into a three-necked flask equipped with a stirring device, dropping funnel, and reflux tube, and placed at room temperature. Stir inside.
3.8 g (0.05 mol) of allyl chloride was dissolved in 50 ml of chloroform and slowly added dropwise at room temperature. After the dropwise addition was completed, the reaction was continued for an additional 2 hours. The precipitated crystals were separated by filtration, and the chloroform layer was washed with 20 ml of water and then dehydrated with magnesium sulfate. After removing chloroform under reduced pressure and concentrating, it was distilled to bp119℃/0.1
7.5 g of α-allylamino-ε-caprolactam was obtained as a mmHg fraction. Yield 74.3%, mp46~7
℃.
【表】
構造は赤外吸収スペクトル（IR）および核磁
気共鳴スペクトル（NMR）によつて確認した。
実施例 ２
α−アミノ−ε−カプロラクタム12.8ｇ（0.1
モル）をベンゼン200mlにとかし、実施例１と同
様の装置に仕込み60℃にて撹拌した。アリルクロ
ライド7.7ｇ（0.1モル）をベンゼン50mlにとか
し、ゆつくり撹拌しながら滴下し、滴下終了後さ
らに２時間反応したのち、析出した結晶をロ別
し、ロ液を全濃縮した。残渣に水を加えてよく撹
き混ぜ、水層と結晶を分離した。水層は濃縮後蒸
留してα−アリルアミノ−ε−カプロラクタム
5.1ｇを得た。水不溶結晶はエタノールで再結晶
し、α−ジアリルアミノ−ε−カプロラクタム
3.9ｇを得た。mp86〜７℃[Table] The structure was confirmed by infrared absorption spectrum (IR) and nuclear magnetic resonance spectrum (NMR). Example 2 α-amino-ε-caprolactam 12.8g (0.1
mol) was dissolved in 200 ml of benzene, charged into the same apparatus as in Example 1, and stirred at 60°C. 7.7 g (0.1 mol) of allyl chloride was dissolved in 50 ml of benzene and slowly added dropwise with stirring. After the addition was completed, the reaction was continued for an additional 2 hours. The precipitated crystals were filtered out and the filtrate was completely concentrated. Water was added to the residue and mixed well to separate the aqueous layer and crystals. The aqueous layer was concentrated and then distilled to produce α-allylamino-ε-caprolactam.
5.1g was obtained. The water-insoluble crystals were recrystallized with ethanol and α-diallylamino-ε-caprolactam
3.9g was obtained. mp86~7℃
【表】
構造はIRおよびNMRによつて確認した。
実施例 ３
α−アミノ−ε−カプロラクタム12.8ｇ（0.1
モル）をクロロホルム100mlにとかし、実施例１
と同様の装置に仕込み、この中ヘカセイソーダ20
％、水溶液50mlを入れ、30℃にて撹拌した。アリ
ルクロライド15.3ｇ（0.2モル）をクロロホルム
50mlにとかし、撹拌しながら滴下した。終了後、
さらに２時間反応したのち、クロロホルム層を分
液した。水層はクロロホルム100mlで抽出し、全
クロロホルム層を一緒にして、全濃縮し、実施例
２と同様にしてα−アリルアミノ−ε−カプロラ
クタム3.4ｇ、α−ジアリルアミノ−ε−カプロ
ラクタム12.5ｇを得た。
実施例 ４
実施例１で製造したα−アリルアミノ−ε−カ
プロラクタム３ｇをエタノールにとかし、エタノ
ール性塩酸でPH４に調整したのち全濃縮した。エ
タノールで再結晶してα−アリルアミノ−ε−カ
プロラクタム塩酸塩を得た。mp246〜７℃
実施例 ５
実施例４と同様にしてα−ジアリルアミノ−ε
−カプロラクタム塩酸塩を得た。mp226〜７℃。[Table] The structure was confirmed by IR and NMR. Example 3 α-amino-ε-caprolactam 12.8g (0.1
Example 1
Pour into a similar device, and add 20% of Hekasei Soda.
% aqueous solution was added thereto, and the mixture was stirred at 30°C. 15.3g (0.2mol) of allyl chloride in chloroform
The mixture was dissolved to 50 ml and added dropwise while stirring. After the end,
After reacting for an additional 2 hours, the chloroform layer was separated. The aqueous layer was extracted with 100 ml of chloroform, all the chloroform layers were combined and concentrated, and the same procedure as in Example 2 was carried out to obtain 3.4 g of α-allylamino-ε-caprolactam and 12.5 g of α-diallylamino-ε-caprolactam. Ta. Example 4 3 g of α-allylamino-ε-caprolactam produced in Example 1 was dissolved in ethanol, adjusted to pH 4 with ethanolic hydrochloric acid, and then completely concentrated. Recrystallization from ethanol gave α-allylamino-ε-caprolactam hydrochloride. mp246~7℃ Example 5 α-diallylamino-ε was prepared in the same manner as in Example 4.
- Caprolactam hydrochloride was obtained. mp226~7℃.
Claims (1)
は−CH2−CH＝CH2を示す） で表わされるα−置換アミノ−ε−カプロラクタ
ム。[Claims] 1. General formula (Here, R 1 is -CH 2 -CH=CH 2 and R 2 is hydrogen or -CH 2 -CH=CH 2. ) α-Substituted amino-ε-caprolactam.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9405578A JPS5520743A (en) | 1978-08-01 | 1978-08-01 | Alpha-substituted amino-epsilon-caprolactam |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9405578A JPS5520743A (en) | 1978-08-01 | 1978-08-01 | Alpha-substituted amino-epsilon-caprolactam |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5520743A JPS5520743A (en) | 1980-02-14 |
| JPS6341907B2 true JPS6341907B2 (en) | 1988-08-19 |
Family
ID=14099850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9405578A Granted JPS5520743A (en) | 1978-08-01 | 1978-08-01 | Alpha-substituted amino-epsilon-caprolactam |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5520743A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005538060A (en) * | 2002-06-12 | 2005-12-15 | ケモセントリックス， インコーポレイテッド | Anti-inflammatory compositions and methods of use |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8621792D0 (en) * | 1986-09-10 | 1986-10-15 | Ici Plc | Hydrodesulphurisation |
-
1978
- 1978-08-01 JP JP9405578A patent/JPS5520743A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005538060A (en) * | 2002-06-12 | 2005-12-15 | ケモセントリックス， インコーポレイテッド | Anti-inflammatory compositions and methods of use |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5520743A (en) | 1980-02-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60308040T2 (en) | Preparation of 1H-imidazo-4,5-C] quinoline-4-amines Ber 1H-imidazo-4,5-C] quinoline-4-phthalimide intermediates | |
| JP2019524770A (en) | Process for producing spiroketal substituted cyclic ketoenols | |
| US4658055A (en) | Method for manufacture of 7-(2,5-dioxocyclopentyl)heptanoic acid derivative | |
| EP0001500A1 (en) | 1-Carbocyclic aryl-2-mono or -bis(alkoxycarbonyl) guanidino ethanes, and methods for their preparation and the preparation therefrom of 4,5-dihydro-2-alkoxycarbonylamino-5-carbocyclic aryl imidazoles | |
| EP0357126B1 (en) | Tetracyclic antidepressants | |
| SU722481A3 (en) | Method of preparing aminoketone derivatives or their salts | |
| SE448459B (en) | 4A, 9B-TRANS-HEXAHYDRO-GAMMA CARBOL COMPOUNDS AS INTERMEDIATES FOR THE PREPARATION OF HEXAHYDRO-GAMMA CARBOL COMPOUNDS | |
| JPS6341907B2 (en) | ||
| US4031108A (en) | 2-Hydroxymethyl-3-benzyloxypyridine-6-epoxyethane | |
| US4704472A (en) | Preparation of an enantiomer of a substituted fluorenyloxyacetic acid | |
| EP1838695A2 (en) | Preparation of ketone amides | |
| CN109232222B (en) | Preparation method of (E) -octyl-4-ene-1, 8-diacid | |
| JP2001521498A (en) | Method for producing O- (3-amino-2-hydroxy-propyl) -hydroxymic acid halide | |
| CN108727214B (en) | Synthetic method of anesthetic bupivacaine impurity | |
| DE60204791T2 (en) | SYNTHESIS OF 4- (PIPERIDYL) (2-PYRIDYL) METHANONE- (E) -O-METHYLOXIM AND ITS SALTS | |
| JP3088561B2 (en) | Method for producing 2,3-diaminopyridines | |
| JP3640319B2 (en) | Method for producing benzamide derivative | |
| KR950005737B1 (en) | Separating method of component from gingkolide complex | |
| DE3815046A1 (en) | 3-CHLORINE-2-METHYLPHENETHYLAMINE DERIVATIVES | |
| JP2767295B2 (en) | Method for producing indole-3-carbonitrile compound | |
| JP2562955B2 (en) | Method for producing (R) -4-hydroxy-5-tetradecic acid- (R)-(+)-α- (1-naphthyl) ethylamine salt | |
| JP3048643B2 (en) | Method for producing 5,7-dihydro-3- [2- {1-benzylpiperidin-4-yl} ethyl] -6H-pyrrolo- [4,5-f] -1,2-benzisoxazol-6-one And intermediates | |
| JPS5838261A (en) | Novel 1,3-disubstituted imidazole derivative and its preparation | |
| JPS63211264A (en) | Production of indolines | |
| JP2005506357A5 (en) |