JPH1129537A - Novel synthetic process for 2-isopropylaminobenzyl alcohol - Google Patents
Novel synthetic process for 2-isopropylaminobenzyl alcoholInfo
- Publication number
- JPH1129537A JPH1129537A JP9182144A JP18214497A JPH1129537A JP H1129537 A JPH1129537 A JP H1129537A JP 9182144 A JP9182144 A JP 9182144A JP 18214497 A JP18214497 A JP 18214497A JP H1129537 A JPH1129537 A JP H1129537A
- Authority
- JP
- Japan
- Prior art keywords
- component
- compound
- formula
- solvent
- reaction
- 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
- 238000000034 method Methods 0.000 title claims description 10
- CAVIKRQEQSWYQE-UHFFFAOYSA-N [2-(propan-2-ylamino)phenyl]methanol Chemical compound CC(C)NC1=CC=CC=C1CO CAVIKRQEQSWYQE-UHFFFAOYSA-N 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 12
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 abstract description 5
- 108091005482 5-HT4 receptors Proteins 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 abstract description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 2
- 229910000085 borane Inorganic materials 0.000 abstract description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 231100000086 high toxicity Toxicity 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- MAEQOIDZBKIVHI-UHFFFAOYSA-N 2,2-dimethyl-1,4-dihydro-3,1-benzoxazine Chemical compound C1=CC=C2COC(C)(C)NC2=C1 MAEQOIDZBKIVHI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000004936 stimulating effect Effects 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000004893 oxazines Chemical class 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical group O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- QTQUJRIHTSIVOF-UHFFFAOYSA-N amino(phenyl)methanol Chemical compound NC(O)C1=CC=CC=C1 QTQUJRIHTSIVOF-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- -1 isopropylaminobenzyl alcohol Chemical compound 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000387 serotonin 5-HT4 receptor agonist Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【０００１】[0001]
【発明が属する技術分野】本発明はアニリン誘導体の新
規な合成法に関し、更に詳しくはセロトニン４受容体刺
激剤としての作用を有するある種のキノリン誘導体製造
のための重要な合成原料を得る方法に関する。The present invention relates to a novel method for synthesizing an aniline derivative, and more particularly to a method for obtaining an important synthetic raw material for producing a certain quinoline derivative acting as a serotonin 4 receptor stimulant. .
【０００２】[0002]
【従来の技術】ジャーナル オブ オルガニック ケミ
ストリィー（Ｊ．Ｏ．Ｃ．），第２８巻，第３２５９頁
（１９６３年）には、アニリンをアセトンと水素化ホウ
素ナトリウムを用いてＮ−イソプロピル化する方法が記
載されている。特開昭５７−３５５７６号公報には２−
アミノベンジルアルコールをアセトンと水素化ホウ素ナ
トリウムを用いてＮ−イソプロピル化する方法が開示さ
れている。特開平２−１３８２６３には、２−アミノベ
ンジルアルコールを塩化カルシウム存在下アセトンと反
応させて得られる１，２−ジヒドロ−２，２−ジメチル
−４Ｈ−３，１−ベンゾオキサジンを水素化ホウ素ナト
リウムにて還元的に開環し該目的化合物を得る方法が開
示されている。以上の方法はいづれも、アニリン誘導体
とアセトンにより生成するシッフ塩基を、ないしはさら
に隣接するヒドロキシ基と分子内閉環したオキサジン誘
導体を反応系内にて経由するか、もしくはオキサジン誘
導体を単離した後、水素化ホウ素ナトリウムにてヒドリ
ド還元することによりアニリン誘導体のＮをイソプロピ
ル化している。2. Description of the Related Art Journal of Organic Chemistry (JOC), vol. 28, p. 3259 (1963) describes that aniline is N-isopropylated using acetone and sodium borohydride. A method is described. JP-A-57-35576 discloses 2-
A method for N-isopropylation of aminobenzyl alcohol using acetone and sodium borohydride is disclosed. JP-A-2-138263 discloses that 1,2-dihydro-2,2-dimethyl-4H-3,1-benzoxazine obtained by reacting 2-aminobenzyl alcohol with acetone in the presence of calcium chloride is sodium borohydride. And a method for reductively opening the ring to obtain the target compound. In any of the above methods, a Schiff base generated by an aniline derivative and acetone, or a further adjacent hydroxy group and an intramolecularly closed oxazine derivative in the reaction system, or after isolating the oxazine derivative, N of the aniline derivative is isopropylated by hydride reduction with sodium borohydride.
【０００３】[0003]
【発明の解決しようとする課題】本発明の目的は、ＷＯ
９５３１４５５に記載された選択的セロトニン４受容体
刺激作用を有するキノリン誘導体の重要な合成原料を得
るための優れた方法を提供することである。従来の方法
においてはいずれも水素化ホウ素ナトリウムを用いてお
り、工業的に生産するためには毒性の強いジボランへの
対策が必要であった。SUMMARY OF THE INVENTION The object of the present invention is to
An object of the present invention is to provide an excellent method for obtaining an important raw material for synthesizing a quinoline derivative having a selective serotonin 4 receptor stimulating action described in U.S. Pat. In all of the conventional methods, sodium borohydride is used, and measures for highly toxic diborane are necessary for industrial production.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、選択的セ
ロトニン４受容体刺激作用を有するキノリン誘導体の製
造に有用な合成原料を得るための有効な製造法の検討を
鋭意重ねた結果、工業的に該目的化合物を得る新しい製
造法を見出し、本発明を完成した。Means for Solving the Problems The present inventors have made intensive studies on an effective production method for obtaining a synthetic raw material useful for producing a quinoline derivative having a selective serotonin 4 receptor stimulating action. The present inventors have found a new process for industrially obtaining the target compound, and have completed the present invention.
【０００５】すなわち本発明は、式That is, the present invention provides
【０００６】[0006]
【化３】 Embedded image
【０００７】（式中、Ｒ1、Ｒ2は同一または各々別途に
水素又は炭素数１〜６のアルキル基を示す）で示される
化合物を金属炭素触媒存在下水素添加することを特徴と
する、式Wherein R 1 and R 2 are the same or separately represent hydrogen or an alkyl group having 1 to 6 carbon atoms, and hydrogenated in the presence of a metal carbon catalyst. formula
【０００８】[0008]
【化４】 Embedded image
【０００９】（Ｒ1、Ｒ2は前記と同意義である。）で示
される化合物の製造方法である。(R 1 and R 2 have the same meanings as described above).
【００１０】[0010]
【発明の実施の形態】本発明において式（１）で表され
る化合物は、式BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, a compound represented by the formula (1)
【００１１】[0011]
【化５】 Embedded image
【００１２】で表される２−アミノベンジルアルコール
を式2-aminobenzyl alcohol represented by the formula:
【００１３】[0013]
【化６】 Embedded image
【００１４】（式中、Ｒ1，Ｒ2は前記と同意義）で表さ
れる化合物と、水、ベンゼン、トルエン、ＴＨＦ等の溶
媒中、酸の存在下０℃から反応溶媒の沸点までの温度範
囲で、１〜４８時間反応させることにより得ることがで
きる。(Wherein R 1 and R 2 are as defined above) and a solvent such as water, benzene, toluene or THF in the presence of an acid from 0 ° C. to the boiling point of the reaction solvent. It can be obtained by reacting in a temperature range for 1 to 48 hours.
【００１５】ついで、式（１）で表される化合物を触媒
存在下還元反応を行い式（２）で表される化合物を得る
ことができる。Next, the compound represented by the formula (1) is subjected to a reduction reaction in the presence of a catalyst to obtain a compound represented by the formula (2).
【００１６】この際、金属炭素触媒は二酸化白金、白金
炭素、ラネーニッケル等であり、触媒の量は原料に対し
１〜２０w/w％が好ましい。用いる溶媒はメタノール、
エタノール、酢酸、水等であり、原料に対し５〜２０倍
量が適当である。反応温度は、通常０℃〜溶媒の沸点ま
でである。その中でもより好ましいのは２０〜５０℃で
ある。反応時間は通常３０分〜４８時間が適当である。
本反応の後処理は触媒を濾去した後に溶媒を留去するの
みである。At this time, the metal carbon catalyst is platinum dioxide, platinum carbon, Raney nickel or the like, and the amount of the catalyst is preferably 1 to 20 w / w% based on the raw material. The solvent used is methanol,
Ethanol, acetic acid, water, etc., and a suitable amount is 5 to 20 times the amount of the raw material. The reaction temperature is usually from 0 ° C to the boiling point of the solvent. Among them, more preferred is 20 to 50 ° C. The appropriate reaction time is usually 30 minutes to 48 hours.
The post-treatment of this reaction is only to distill off the solvent after filtering off the catalyst.
【００１７】[0017]
【発明の効果】本発明により毒性の強いボランを発生す
る水素化ホウ素ナトリウムを使用することなくＷＯ９５
３１４５５に記載された選択的セロトニン４受容体刺激
作用を有するキノリン誘導体の重要な合成原料を得られ
る。According to the present invention, WO95 can be obtained without using sodium borohydride which generates highly toxic borane.
An important raw material for the synthesis of a quinoline derivative having a selective serotonin 4 receptor stimulating action described in 31455 can be obtained.
【００１８】[0018]
【実施例】以下、実施例、参考例を挙げて本発明を更に
具体的に説明する。EXAMPLES The present invention will be described more specifically with reference to examples and reference examples.
【００１９】実施例１ ５Ｌの４つ口フラスコに５００ｇ（４．６３ｍｏｌ）の
２−アミノベンジルアルコールを入れ、水４０００ｇと
氷酢酸８．３ｇ（０．１４ｍｏｌ、０．０３ｅｑ）を加
えて攪拌した懸濁液に、アセトン４０３ｇ（６．９４ｍ
ｏｌ、１．５ｅｑ）を１０分かけて滴下した。室温で１
時間攪拌した後、氷冷下で１時間攪拌し、得られた結晶
を濾過して、水１５００ｇで洗浄した。結晶を風乾して
７００ｇ（４．２９ｍｏｌ、収率９３％）の１，２−ジ
ヒドロ−２，２−ジメチル−４Ｈ−３，１−ベンゾオキ
サジンを得た。Example 1 A 5-liter four-necked flask was charged with 500 g (4.63 mol) of 2-aminobenzyl alcohol, and 4000 g of water and 8.3 g (0.14 mol, 0.03 eq) of glacial acetic acid were added and stirred. 403 g of acetone (6.94 m) was added to the suspension.
ol, 1.5 eq) was added dropwise over 10 minutes. 1 at room temperature
After stirring for 1 hour, the mixture was stirred for 1 hour under ice cooling, and the obtained crystals were filtered and washed with 1500 g of water. The crystals were air-dried to obtain 700 g (4.29 mol, yield 93%) of 1,2-dihydro-2,2-dimethyl-4H-3,1-benzoxazine.
【００２０】実施例２ 回転攪拌式２００ｍｌオートクレーブに化合物２を７ｇ
（０．０４３ｍｏｌ）とメタノール５６ｇ及び５％白金
炭素触媒０．１４ｇを入れ、密閉してオートクレーブ中
の空気を窒素ガスで置換し、続いて水素ガスで置換し
た。水素圧力を３０ｋｇ／ｃｍ2、反応温度を４０℃に
保ちながら２時間攪拌した。反応終了後、冷却してから
触媒を濾過して除き、得られた反応液を濃縮した後、ト
ルエンに溶解した。トルエン溶液を水で洗浄し、乾燥し
た後、溶媒を留去して５．６ｇ（０．０３４ｍｏｌ，収
率７９％）のイソプロピルアミノベンジルアルコールを
得た。Example 2 7 g of compound 2 was placed in a 200 ml autoclave of a rotary stirring type.
(0.043 mol), 56 g of methanol and 0.14 g of a 5% platinum carbon catalyst were put in the vessel, and the air in the autoclave was closed and replaced with nitrogen gas, and then replaced with hydrogen gas. The mixture was stirred for 2 hours while maintaining the hydrogen pressure at 30 kg / cm 2 and the reaction temperature at 40 ° C. After completion of the reaction, the reaction solution was cooled, filtered to remove the catalyst, and the obtained reaction solution was concentrated and then dissolved in toluene. After the toluene solution was washed with water and dried, the solvent was distilled off to obtain 5.6 g (0.034 mol, yield 79%) of isopropylaminobenzyl alcohol.
【００２１】ガスクロマトグラフィーで分析したとこ
ろ、面積百分率で１，２−ジヒドロ−２，２−ジメチル
−４Ｈ−３，１−ベンゾオキサジンが１．０％、２−イ
ソプロピルアミノベンジルアルコールは９８．６％であ
った。Analysis by gas chromatography revealed that 1,2-dihydro-2,2-dimethyl-4H-3,1-benzoxazine was 1.0% in area percentage and 98.6 in 2-isopropylaminobenzyl alcohol in terms of area percentage. %Met.
【００２２】実施例３ 回転攪拌式２００ｍｌオートクレーブに２−アミノベン
ジルアルコールを７ｇ（０．０５７ｍｏｌ）とメタノー
ル５６ｇ、氷酢酸０．３４ｇ（０．００５７ｍｏｌ、
０．１ｅｑ）、アセトン６．３ｍｌ（０．０８６ｍｏ
ｌ、１．５ｅｑ）及び５％白金炭素触媒０．３５ｇを入
れ、密閉してオートクレーブ中の空気を窒素ガスで置換
し、室温で２時間攪拌した。続いて水素ガスで置換して
水素圧力を３０Ｋｇ／ｃｍ2、反応温度を４０℃に保ち
ながら２．５時間攪拌した。反応終了後、冷却してから
触媒を濾過して除き、得られた反応液を濃縮した後トル
エンに溶解した。トルエン溶液を水で洗浄し、乾燥した
後溶媒を留去して、７．６ｇ（０。０４６ｍｏｌ，収率
８１％）の２−イソプロピルアミノベンジルアルコール
を得た。ガスクロマトグラフィーで分析したところ、面
積百分率で２−アミノベンジルアルコール１が２．５
％、２−イソプロピルアミノベンジルアルコールは９
５．２％であった。Example 3 In a rotary stirring type 200 ml autoclave, 7 g (0.057 mol) of 2-aminobenzyl alcohol, 56 g of methanol, 0.34 g (0.0057 mol,
0.1eq), acetone 6.3ml (0.086mo
1, 1.5 eq) and 0.35 g of a 5% platinum carbon catalyst were put in, sealed, and the air in the autoclave was replaced with nitrogen gas, followed by stirring at room temperature for 2 hours. Subsequently, the mixture was replaced with hydrogen gas and stirred for 2.5 hours while keeping the hydrogen pressure at 30 kg / cm 2 and the reaction temperature at 40 ° C. After completion of the reaction, the reaction mixture was cooled, filtered to remove the catalyst, and the obtained reaction solution was concentrated and dissolved in toluene. The toluene solution was washed with water, dried and then the solvent was distilled off to obtain 7.6 g (0.046 mol, 81% yield) of 2-isopropylaminobenzyl alcohol. When analyzed by gas chromatography, 2-aminobenzyl alcohol 1 was 2.5% by area percentage.
%, 2-isopropylaminobenzyl alcohol is 9%
It was 5.2%.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 福島 浩 東京都豊島区高田３丁目24番１号 大正製 薬株式会社内 ────────────────────────────────────────────────── ─── Continued on the front page (72) Inventor Hiroshi Fukushima 3-24-1, Takada, Toshima-ku, Tokyo Taisho Pharmaceutical Co., Ltd.
Claims (2)
数１〜６のアルキル基を示す。）で示される化合物を金
属炭素触媒存在下水素添加することを特徴とする 【化２】 （Ｒ1、Ｒ2は前記と同意義である。）で示される化合物
の製造方法。[Claim 1] (Wherein, R 1 and R 2 are the same or separately represent hydrogen or an alkyl group having 1 to 6 carbon atoms), and hydrogenated in the presence of a metal carbon catalyst. ] (R 1 and R 2 are as defined above).
記載の製造方法。2. The method according to claim 1 , wherein both R 1 and R 2 are methyl groups.
The manufacturing method as described.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9182144A JPH1129537A (en) | 1997-07-08 | 1997-07-08 | Novel synthetic process for 2-isopropylaminobenzyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9182144A JPH1129537A (en) | 1997-07-08 | 1997-07-08 | Novel synthetic process for 2-isopropylaminobenzyl alcohol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH1129537A true JPH1129537A (en) | 1999-02-02 |
Family
ID=16113135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9182144A Pending JPH1129537A (en) | 1997-07-08 | 1997-07-08 | Novel synthetic process for 2-isopropylaminobenzyl alcohol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH1129537A (en) |
-
1997
- 1997-07-08 JP JP9182144A patent/JPH1129537A/en active Pending
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