JPH01301655A - Production of 1-benzyl-3-benzylaminopyrrolidines - Google Patents
Production of 1-benzyl-3-benzylaminopyrrolidinesInfo
- Publication number
- JPH01301655A JPH01301655A JP63132346A JP13234688A JPH01301655A JP H01301655 A JPH01301655 A JP H01301655A JP 63132346 A JP63132346 A JP 63132346A JP 13234688 A JP13234688 A JP 13234688A JP H01301655 A JPH01301655 A JP H01301655A
- Authority
- JP
- Japan
- Prior art keywords
- benzyl
- hensyl
- formula
- hydrogen
- present
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- BHEXKVGLZMEJRQ-UHFFFAOYSA-N n,1-dibenzylpyrrolidin-3-amine Chemical class C=1C=CC=CC=1CNC(C1)CCN1CC1=CC=CC=C1 BHEXKVGLZMEJRQ-UHFFFAOYSA-N 0.000 title description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 11
- DHGMDHQNUNRMIN-UHFFFAOYSA-N 1-benzylpyrrolidin-3-one Chemical class C1C(=O)CCN1CC1=CC=CC=C1 DHGMDHQNUNRMIN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims abstract 8
- OKAYLLGQULCTNO-UHFFFAOYSA-N n-benzylpyrrolidin-1-amine Chemical class C=1C=CC=CC=1CNN1CCCC1 OKAYLLGQULCTNO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000012442 inert solvent Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 4
- -1 1,2,4-trisubstituted-butane Chemical class 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KWFATJMDSMSKPA-UHFFFAOYSA-N 1-butylpyrrolidin-3-one Chemical compound CCCCN1CCC(=O)C1 KWFATJMDSMSKPA-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical class NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
産 の １
本発明は１−ベンジル−３−ヘンシルアミノピロリジン
類の製造法に関する。１−ヘンシル−３−ヘンシルアミ
ノピロリジン類は医薬合成用の中間体として極めて重要
な化合物である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 1-benzyl-3-hensylaminopyrrolidines. 1-hensyl-3-hensylaminopyrrolidines are extremely important compounds as intermediates for pharmaceutical synthesis.
１又肢Ｉ
従来、１−ヘンシル−３−ヘンシルアミノピロリジンの
製造法としては、１．２．１ｌＬｌり置換−ブタン（置
換基はハロゲン原子又はＯＲ’ （Ｒ’はアルカンス
ルホニル基あるいは芳香族スルボニル基を示す〉）にヘ
ンシルアミンを反応させる方法が知られている（特開昭
６２−８７５６５）。Conventionally, 1-hensyl-3-hensylaminopyrrolidine has been produced using 1.2.1lLl-substituted-butane (substituent is halogen atom or A method is known in which a sulfonyl group) is reacted with hensylamine (Japanese Unexamined Patent Publication No. 87565/1983).
ｔ”’ 」ユニ」１１
この従来方法では、次の様な欠点があり、工業的製造法
としては十分なものとはいいがたい。t'''``Uni'' 11 This conventional method has the following drawbacks and cannot be said to be sufficient as an industrial manufacturing method.
■原料として１，２．４−）リハロゲノブタンを用いた
場合、このハロゲンによる腐食のために、安価な鉄製製
造装置を使用して１−へンジルアミノビロリジンを製造
しがたく、製造装置に対する材質上の制限がある。さら
に、精製１−ヘンシル−３−ヘンシルアミノピロリジン
は反応液を抽出、濃縮、蒸留を行ない、次いで留出した
粗製品を再蒸留することによって得られる。このように
精製１−ヘンシル−３−ヘンシルアミノピロリジンを得
るには、かなり繁雑な処理を必要とする。■When using 1,2.4-)rehalogenobutane as a raw material, it is difficult to produce 1-hendylaminopyrrolidine using inexpensive iron production equipment due to corrosion caused by this halogen, and There are limitations due to the material. Further, purified 1-hensyl-3-hensylaminopyrrolidine can be obtained by extracting, concentrating and distilling the reaction solution, and then redistilling the distilled crude product. Obtaining purified 1-hensyl-3-hensylaminopyrrolidine in this way requires quite complicated treatments.
■置換基がＯＲ’ 、又はＯＲ’とハロゲン原子である
１、２．４−トリ置換−ブタンを原料として用いた場合
、精製１−ヘンシル−３−ヘンシルアミノピロリジンを
得るには、１，２．４−）リハロゲノブタンの場合より
も一層繁雑な処理を必要とする。すなわち、反応液を抽
出、濃縮、蒸留し、さらに得られた油状物を塩酸処理し
、次いて抽出、蒸留して精製１−ヘンシル−３−ヘンシ
ルアミノピロリジンを得ている。(2) When 1,2,4-trisubstituted-butane in which the substituent is OR' or OR' and a halogen atom is used as a raw material, to obtain purified 1-hensyl-3-hensylaminopyrrolidine, 1, 2.4-) Requires more complicated processing than in the case of rehalogenobutane. That is, the reaction solution is extracted, concentrated, and distilled, and the resulting oil is treated with hydrochloric acid, and then extracted and distilled to obtain purified 1-hensyl-3-hensylaminopyrrolidine.
本発明の目的は、かかる欠点を克服した１−ヘンシル−
３−ヘンシルアミノピロリジン類の新規な製造法を提供
することにある。The object of the present invention is to overcome these drawbacks by
The object of the present invention is to provide a novel method for producing 3-hensylaminopyrrolidines.
皿」Ｌ迄］Ｌ決Ｗ引の」ｋ段
本発明者は鋭意研究を行なった結果、パラジウム触媒の
存在下に、１−ベンジル−３−ピロリドン類とヘンシル
アミン及び水素を反応させると、反応液から触媒をろ側
稜、単蒸留を行なうのみて、高純度の１−ヘンシル−３
−ベンジルアミノピロリジン類を高収率で製造できるこ
とを見出し、本発明を完成するに至ったものである。As a result of intensive research, the inventors have found that when 1-benzyl-3-pyrrolidones are reacted with hensylamine and hydrogen in the presence of a palladium catalyst, the reaction solution is High purity 1-Hensyl-3 is obtained by simply distilling the catalyst from the filter side and performing simple distillation.
- It was discovered that benzylaminopyrrolidines can be produced in high yield, and the present invention was completed.
すなわち、本発明はパラジウム触媒の存在下、示される
１−ヘンシル−３−ピロリドン類、ヘンシルアミン、及
び水素を反応させることを特徴と（式中、Ｒは前記と同
し）で示される１−ヘンレジルー３−ヘンシルアミノピ
ロリジン類の製造法である。That is, the present invention is characterized by reacting the 1-hensyl-3-pyrrolidones shown, hensylamine, and hydrogen in the presence of a palladium catalyst (wherein R is the same as above). This is a method for producing 3-hensylaminopyrrolidines.
本発明の一般式（１）及び（２）におけるＲは低級アル
キル基を示し、具体的にはメチル基、エチル基、プロピ
ル基、ブチル基、ｔｅｒｔ−ブチル基なとの炭素数１〜
４のアルキル基が挙げられる。R in the general formulas (1) and (2) of the present invention represents a lower alkyl group, specifically a methyl group, an ethyl group, a propyl group, a butyl group, a tert-butyl group, etc. having 1 to 1 carbon atoms.
4 alkyl groups are mentioned.
本発明の一般式（１）で示される１−ヘンシル−３−ピ
ロリドン類としては、例えば１−ヘンシル−３−ピロリ
ドン、１−へフジルー２−メチル−３−ピロリドン、１
−ヘンシル−４−メチル−３−ピロリドン、１−ヘンシ
ル−４−エチル−３−ピロリドン、１−ヘンシル−４−
ブチル−３−ピロリドンなどが挙げられる。Examples of the 1-hensyl-3-pyrrolidones represented by the general formula (1) of the present invention include 1-hensyl-3-pyrrolidone, 1-hefzi-2-methyl-3-pyrrolidone, 1-hensyl-3-pyrrolidone,
-hensyl-4-methyl-3-pyrrolidone, 1-hensyl-4-ethyl-3-pyrrolidone, 1-hensyl-4-
Examples include butyl-3-pyrrolidone.
本発明において、例えば出発原料の−っである１−ベン
ジル−３−ピロリドンは一般にＮ−ベンジル−Ｎ−力ル
ボキシメチルーβ−アラニン・ジアルキルエステルを金
属アルコキシドの存在下で環化し、次いて酸性条件下で
脱炭酸反応を行ない好収率て製造できる。In the present invention, for example, 1-benzyl-3-pyrrolidone, which is the starting material, is generally obtained by cyclizing N-benzyl-N-hydroxymethyl-β-alanine dialkyl ester in the presence of a metal alkoxide, and then under acidic conditions. It can be produced in good yield by carrying out decarboxylation reaction.
本発明で用いられるヘンシルアミンの使用量は、一般式
（１）で表わされる１−ヘンシル−３−ピロリドン類に
対して等モル以上あれば十分であるが、好ましくは１〜
５倍モルの範囲である。It is sufficient that the amount of hensylamine used in the present invention is at least equimolar to the 1-hensyl-3-pyrrolidone represented by the general formula (1), but preferably 1 to
The range is 5 times the mole.
本発明において、触媒としてパラジウム触媒を用いるこ
とが重要である。他の水素化触媒として、例えばラネー
ニッケルを用いると、パラジウム触媒に比へて本発明の
目的物を極めて低い収率てしか得ることができない。In the present invention, it is important to use a palladium catalyst as the catalyst. When Raney nickel, for example, is used as another hydrogenation catalyst, the object of the present invention can only be obtained in a very low yield compared to a palladium catalyst.
本発明で用いられるパラジウム触媒は、工業的に市販さ
れているアルミナ、珪藻土、白土又は活性炭等に担持さ
せたものが挙げられる。又、パラジウム触媒にはニッケ
ル等の他の金属を含有してもよい。パラジウム触媒の使
用量としては特に制限されないが、例えは５％パラジウ
ム／カーボンなら原料の１−ベンジル−３−ピロリドン
類に対して０．１％〜２０重量パーセントの範囲が好適
である。Examples of the palladium catalyst used in the present invention include those supported on commercially available alumina, diatomaceous earth, clay, or activated carbon. Further, the palladium catalyst may contain other metals such as nickel. The amount of the palladium catalyst to be used is not particularly limited, but for example, if it is 5% palladium/carbon, it is preferably in the range of 0.1% to 20% by weight based on the 1-benzyl-3-pyrrolidone raw material.
本発明において、反応温度は特に限定されないが、２０
〜１００℃の範囲が好適である。反応温度が２０℃より
低いと反応速度が著しく遅くなり、工業的には不利とな
る。又、反応温度は１００℃より高いと反応速度は速い
が高沸点の副生成物ができ、収率が低下する。In the present invention, the reaction temperature is not particularly limited, but 20
A range of 100°C to 100°C is preferred. If the reaction temperature is lower than 20°C, the reaction rate will be extremely slow, which is industrially disadvantageous. On the other hand, if the reaction temperature is higher than 100° C., although the reaction rate is high, by-products with high boiling points are produced and the yield is reduced.
本発明は通常加圧下で反応を行ない、水素の分圧として
は０．５〜１００ｋｇ／ｃｍ２の範囲が好ましい。所定
の圧力を維持するには外から供給する水素カスでコント
ロールし、もし水素が消費されて内圧が下がれは水素を
補給して、所定内圧を維持することができる。In the present invention, the reaction is usually carried out under pressure, and the partial pressure of hydrogen is preferably in the range of 0.5 to 100 kg/cm2. To maintain a predetermined pressure, it is controlled by hydrogen gas supplied from outside, and if hydrogen is consumed and the internal pressure drops, hydrogen can be replenished to maintain the predetermined internal pressure.
本発明の方法は反応溶媒を用いなくても実施できるが、
反応溶媒としてヘンセン、トルエン、キシレン等の不活
性溶媒の使用は、本発明の目的物の収率が向上し、好ま
しい。Although the method of the present invention can be carried out without using a reaction solvent,
It is preferable to use an inert solvent such as Hensen, toluene, xylene, etc. as a reaction solvent because it improves the yield of the target product of the present invention.
本発明において、反応時間は通常１８時間程度で十分で
ある。In the present invention, a reaction time of about 18 hours is usually sufficient.
このようにして生成された１−ヘンシル−３−ヘンシル
アミノピロリジン類は、−船釣な分離手段で容易に単離
精製できる。例えは、反応液をろ過してパラジウム触媒
を除去し、ろ液を単蒸留することにより単離精製される
。The 1-hensyl-3-hensyl aminopyrrolidines thus produced can be easily isolated and purified by a boat-type separation method. For example, the reaction solution is filtered to remove the palladium catalyst, and the filtrate is isolated and purified by simple distillation.
犬差Ｊｌ
以下に、実施例を挙げて本発明を具体的に説明するが、
本発明はこれらの実施例に限定されるものではない。Inugashi Jl The present invention will be specifically explained below with reference to Examples.
The present invention is not limited to these examples.
実」１例Ｊ
１リツトルの電磁攪はん式オートクレーブに、１−ヘン
シル−３−ピロリドン１２０ｇ、Ｊ＼ンジルアミン２２
０ｇ及び５％パラジウム／カーボン３ｇを仕込み、容器
内を水素置換した後、内温を５０℃に昇温した。次に、
同温で反応圧２０ｋｇ／ｃｍ２を保ちながら、８時間で
水素１８リツトルを流入した。反応後、オートクレーブ
を室温に冷却し、内容物を取り出して触媒をろ別した。1 example J In a 1 liter electromagnetic stirring autoclave, 120 g of 1-hensyl-3-pyrrolidone, 22
After charging 0g and 3g of 5% palladium/carbon and purging the inside of the container with hydrogen, the internal temperature was raised to 50°C. next,
While maintaining the same temperature and reaction pressure of 20 kg/cm2, 18 liters of hydrogen was introduced over 8 hours. After the reaction, the autoclave was cooled to room temperature, the contents were taken out, and the catalyst was filtered off.
ろ液を単蒸留したところ、塔頂温度１９２〜１９３℃／
１、ＯｍｍＨｇてＧＣ純度９９，３％の１−ヘンシル−
３−ヘンシルアミノピロリジン１４４ｇを得た。When the filtrate was simply distilled, the top temperature was 192-193℃/
1. 1-Hensyl with GC purity of 99.3% at OmmHg
144 g of 3-hensylaminopyrrolidine was obtained.
この前後の留分を合わせると、１−ヘンシル−３−ヘン
シルアミノピロリジンの収率は８８％てあった。When the fractions before and after this were combined, the yield of 1-hensyl-3-hensylaminopyrrolidine was 88%.
’ＬｊＬＭユ
実施例１と同し反応器に１−ヘンシル−３−ピリドン１
２０ｇ、ノ＼ンジルアミン２２０ｇ、）ルエン２４０ｇ
及び５％パラジウム／カーボン３ｇを仕込み、容器内を
水素置換した後、内温５０’Ｃ１内圧４０ ｋｇ ／
ｃｍ２を保ちながら水素１８リツトルを４時間で流入し
た。反応液を実施例１と同様に処理して、ＧＣ純度９９
．５％の１−ヘンシル−３−ヘンシルアミノピロリジン
１７０ｇを得て、その前後の留分を合わせると１−ヘン
シル−３−ヘンシルアミノピロリジンの収率は９５．０
％となった。'LjLMU 1-hensyl-3-pyridone 1 was added to the same reactor as in Example 1.
20g, nonylamine 220g, ) toluene 240g
After charging 3 g of 5% palladium/carbon and replacing the inside of the container with hydrogen, the internal temperature was 50'C1 and the internal pressure was 40 kg/
18 liters of hydrogen was flowed in over 4 hours while maintaining the pressure of cm2. The reaction solution was treated in the same manner as in Example 1, and the GC purity was 99.
．． When 170 g of 5% 1-hensyl-3-hensylaminopyrrolidine was obtained and the fractions before and after were combined, the yield of 1-hensyl-3-hensylaminopyrrolidine was 95.0.
%.
支隻朋Ｊ
１−ベンジル−３−ピロリドンの代わりに、１−ヘンシ
ル−４−メチル−３−ピロリドン１２９ｇを使用した他
は、実施例１と同様に操作し、ＧＣ純度９９．０％の１
−ヘンシル−４−メチル−３−ヘンシルアミノピロリジ
ン１５３ｇ（収率８０％）を得た。Shifuno J The same procedure as in Example 1 was carried out except that 129 g of 1-hensyl-4-methyl-3-pyrrolidone was used instead of 1-benzyl-3-pyrrolidone.
-Hensyl-4-methyl-3-hensylaminopyrrolidine 153g (yield 80%) was obtained.
発」ＬＱ」Ｌ果
本発明の方法によれば、従来技術に比べて極めて簡単な
分離精製手段で、高純度１−ベンジル−３−ベンジルア
ミノピロリジン類が高収率で得ることができ、又、従来
技術のように出発原料にハロゲン化物を用いないので、
製造装置の材質的制限がなく、本発明は工業的に極めて
有用なものである。According to the method of the present invention, highly purified 1-benzyl-3-benzylaminopyrrolidines can be obtained in high yield with extremely simple separation and purification means compared to conventional techniques, and , since no halide is used as a starting material unlike the conventional technology,
The present invention is industrially extremely useful since there are no limitations on the material of the manufacturing equipment.
特許出願人 広栄化学工業株式会社 ｌＯ−Patent applicant: Koei Chemical Industry Co., Ltd. lO-
Claims (1)
学式、表等があります▼（１） （式中、Ｒは水素原子又は低級アルキル基を示す）で示
される１−ベンジル−３−ピロリドン類、ベンジルアミ
ン及び水素を反応させることを特徴とする一般式（２）
： ▲数式、化学式、表等があります▼（２） （式中、Ｒは前記と同じ）で示される１−ベンジル−３
−ベンジルアミノピロリジン類の製造法。[Claims] In the presence of a palladium catalyst, 1 represented by the general formula (1): ▲ Numerical formula, chemical formula, table, etc. ▼ (1) (in the formula, R represents a hydrogen atom or a lower alkyl group) - General formula (2) characterized by reacting benzyl-3-pyrrolidones, benzylamine, and hydrogen
: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(2) 1-benzyl-3 represented by (in the formula, R is the same as above)
- A method for producing benzylaminopyrrolidines.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63132346A JP2683809B2 (en) | 1988-05-30 | 1988-05-30 | Process for producing 1-benzyl-3-benzylaminopyrrolidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63132346A JP2683809B2 (en) | 1988-05-30 | 1988-05-30 | Process for producing 1-benzyl-3-benzylaminopyrrolidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01301655A true JPH01301655A (en) | 1989-12-05 |
| JP2683809B2 JP2683809B2 (en) | 1997-12-03 |
Family
ID=15079197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63132346A Expired - Lifetime JP2683809B2 (en) | 1988-05-30 | 1988-05-30 | Process for producing 1-benzyl-3-benzylaminopyrrolidines |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2683809B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008050307A (en) * | 2006-08-25 | 2008-03-06 | Koei Chem Co Ltd | Method for producing piperidine compound |
-
1988
- 1988-05-30 JP JP63132346A patent/JP2683809B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008050307A (en) * | 2006-08-25 | 2008-03-06 | Koei Chem Co Ltd | Method for producing piperidine compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2683809B2 (en) | 1997-12-03 |
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