KR840002343A - Method for preparing benzyl alcohol derivative - Google Patents

Method for preparing benzyl alcohol derivative Download PDF

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KR840002343A
KR840002343A KR1019820005098A KR820005098A KR840002343A KR 840002343 A KR840002343 A KR 840002343A KR 1019820005098 A KR1019820005098 A KR 1019820005098A KR 820005098 A KR820005098 A KR 820005098A KR 840002343 A KR840002343 A KR 840002343A
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compound
iii
formula
carried out
benzyl alcohol
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KR1019820005098A
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Korean (ko)
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KR870000471B1 (en
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이쿠오 이이지마
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마츠하라 이치로오
다나베 세이야쿠 가부시끼가이샤
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
    • C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C07C215/60—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
    • C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
    • C07C217/70—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters

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  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

내용 없음.No content.

Description

벤질알콜 유도체의 제조방법Method for preparing benzyl alcohol derivative

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (3)

(a)하기 구조식(Ⅱ)의 아세토페논 유도체를 염화티오닐과 반응하고, (b)그 결과 얻어진 생성물을 3,4-디메톡시펜에틸아민과 반응하여 하기 구조식(Ⅲ)의 티오아세트 아마이드 유도체를 얻은 다음. (c)-ⅰ)화합물(Ⅲ)은 환원적으로 탈황하거나, -ⅱ)화합물(Ⅲ)을 알킬화하여 하기 구조식(Ⅳ)의 아세토페논 유도체를 얻은다음, 화합물(Ⅳ)를 환원적으로 탈황하거나, 또는 -ⅲ)화합물(Ⅲ)을 환원하여 하기 구조식(Ⅴ)의 벤질 알콜 유도체를 얻은다음, 화합물(Ⅴ)를 알킬롸하여 하기 구조식(Ⅵ)의 벤질알콜 유도체를 얻은후, 화합물(Ⅵ)을 환원적으로 탈황한 다음. (d) 필요하다면, 얻어진 하기 구조식(Ⅰ)의 벤질 알콜유도체를 약리적으로 허용되는 그의 산부가염으로 전환하는 것을 특징으로 하는 하기 구조식(Ⅰ)의 벤질알콜 유도체 또는 약리적으로 허용되는 그의 산부가염을 제조하는 방법.(a) acetophenone derivative of formula (II) is reacted with thionyl chloride, and (b) the resulting product is reacted with 3,4-dimethoxyphenethylamine to form a thioacetamide derivative of formula (III) Then obtained. (c) -iii) Compound (III) is reductively desulfurized, or -ii) Alkylation of Compound (III) yields an acetophenone derivative of formula (IV), followed by reductive desulfurization of Compound (IV), or Or (iii) reducing compound (III) to obtain a benzyl alcohol derivative of formula (V), followed by alkylation of compound (V) to obtain a benzyl alcohol derivative of formula (VI), followed by compound (VI) Reductively desulfurized. (d) if necessary, preparing a benzyl alcohol derivative of formula (I) or a pharmacologically acceptable acid addition salt thereof, characterized by converting the obtained benzyl alcohol derivative of formula (I) to a pharmacologically acceptable acid addition salt thereof. How to. 상기식에서, R1은 수소 또는 알칼킬이고, R2는 수소, 알카노일 또는 아랄킬이고, R3는 알킬이다.Wherein R 1 is hydrogen or alkalkyl, R 2 is hydrogen, alkanoyl or aralkyl and R 3 is alkyl. 제1항에 있어서, 화합물(Ⅲ)의 환원적 탈황반응이 용매중금속 할로겐화물(예, 염화니켈, 염화제일철 염화제일주석, 염화아연 및 염화코발트)존재하에 환원제로서 알카리금속 보로하이드라이드를 사용하므로써 실시되고 ; 화합물(Ⅲ) 또는 화합물(Ⅴ)의 알킬화는 용매중 산수용체의 존재여부에 관계없이 알킬화제(예, 저급알킬 할로겐화물, 저급 알킬옥소늄프롤오로보레이트 및 디(저급알킬)황산염)을 사용하므로써 실시되고 ; 화합물(Ⅳ) 또는 (Ⅵ)의 환원적 탈황반응은 용매중에서 환원제(예, 알카리금속 보로하이드라이드 및 리튬 알루미늄하이드라이드)를 사용하므로써 실시되는 것을 특징으로 하는 방법.The method of claim 1, wherein the reductive desulfurization of compound (III) is carried out by using an alkali metal borohydride as reducing agent in the presence of a metal halide in the solvent (e.g. nickel chloride, ferrous chloride, zinc chloride and cobalt chloride). Is carried out; Alkylation of compound (III) or compound (V) is carried out by the use of alkylating agents (e.g. lower alkyl halides, lower alkyl oxonium proboroborate and di (lower alkyl) sulfate) regardless of the presence of acid acceptors in the solvent. Being; Reductive desulfurization of compound (IV) or (VI) is carried out by using reducing agents (eg, alkali metal borohydride and lithium aluminum hydride) in a solvent. 제2항에 있어서, 화합물(Ⅲ)의 환원적 탈황반응이 20°- 50℃에서 실시되고 ; 화합물(Ⅲ) 또는 (Ⅴ)의 알킬화반응이 0°- 30℃에서 실시되며 ; 화합물(Ⅳ) 또는 (Ⅵ)의 환원적 탈황반응이 0°- 30℃에서 실시되는 것을 특징으로 하는 방법.The process according to claim 2, wherein the reductive desulfurization of compound (III) is carried out at 20 ° -50 ° C; Alkylation of compound (III) or (V) is carried out at 0 ° -30 ° C .; Reductive desulfurization of compound (IV) or (VI) is carried out at 0 ° -30 ° C. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR828205098A 1981-11-12 1982-11-11 Process for preparing benzylalcohol derivatives KR870000471B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP56181951A JPS5883661A (en) 1981-11-12 1981-11-12 Preparation of benzyl alcohol derivative
JP181951 1981-11-12

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KR840002343A true KR840002343A (en) 1984-06-25
KR870000471B1 KR870000471B1 (en) 1987-03-11

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JP (1) JPS5883661A (en)
KR (1) KR870000471B1 (en)
AT (1) AT382866B (en)
CA (1) CA1196342A (en)
CH (1) CH650247A5 (en)
DK (1) DK163660C (en)
ES (1) ES8401013A1 (en)
HU (1) HU189190B (en)
IT (1) IT1191227B (en)
SE (1) SE454775B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4579972A (en) * 1983-04-28 1986-04-01 Smithkline Beckman Corporation Intermediates for preparing secondary amines
JPH0735693U (en) * 1993-12-14 1995-07-04 協和電機化学株式会社 Seal for sealing the butt of glass doors
US7985168B2 (en) 2009-03-25 2011-07-26 Graa Innovations, Llc Power stride apparatus and method of training therefor

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5310974B2 (en) * 1974-06-10 1978-04-18
JPS6241829Y2 (en) * 1980-03-28 1987-10-26

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AT382866B (en) 1987-04-27
DK502682A (en) 1983-05-13
SE8206352L (en) 1983-05-13
CH650247A5 (en) 1985-07-15
IT1191227B (en) 1988-02-24
JPS6121620B2 (en) 1986-05-28
ES517297A0 (en) 1983-12-01
SE8206352D0 (en) 1982-11-09
DK163660B (en) 1992-03-23
ATA409882A (en) 1986-09-15
JPS5883661A (en) 1983-05-19
ES8401013A1 (en) 1983-12-01
SE454775B (en) 1988-05-30
KR870000471B1 (en) 1987-03-11
HU189190B (en) 1986-06-30
IT8268332A0 (en) 1982-11-11
DK163660C (en) 1992-08-17
CA1196342A (en) 1985-11-05

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