JPS5753440A - Preparation of 4-aminomethylcyclohexanecarboxylic acid and its mineral acid salt - Google Patents

Preparation of 4-aminomethylcyclohexanecarboxylic acid and its mineral acid salt

Info

Publication number
JPS5753440A
JPS5753440A JP55128962A JP12896280A JPS5753440A JP S5753440 A JPS5753440 A JP S5753440A JP 55128962 A JP55128962 A JP 55128962A JP 12896280 A JP12896280 A JP 12896280A JP S5753440 A JPS5753440 A JP S5753440A
Authority
JP
Japan
Prior art keywords
acid
mineral acid
aminomethylcyclohexanecarboxylic
mineral
preparation
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
Application number
JP55128962A
Other languages
Japanese (ja)
Other versions
JPS5951934B2 (en
Inventor
Masaaki Takahashi
Takashi Yamauchi
Akira Iizuka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kureha Corp
Original Assignee
Kureha Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kureha Corp filed Critical Kureha Corp
Priority to JP55128962A priority Critical patent/JPS5951934B2/en
Priority to CA000385915A priority patent/CA1179369A/en
Priority to FR8117501A priority patent/FR2490218A1/en
Priority to GB8128010A priority patent/GB2084145B/en
Priority to DE3137092A priority patent/DE3137092C2/en
Publication of JPS5753440A publication Critical patent/JPS5753440A/en
Publication of JPS5951934B2 publication Critical patent/JPS5951934B2/en
Expired legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/46—Ruthenium, rhodium, osmium or iridium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

PURPOSE: To prepare the titled compound useful as an intermediate of pharmaceuticals, easily, in a one-step reaction, in high yield, by the catalytic reduction of 4-hydroxyiminomethylbenzoic acid in a medium comprising water containing a mineral acid, using a Pd-Pt-Rh catalyst.
CONSTITUTION: 4-Hydroxyiminomethylbenzoic acid is catalytically reduced in a medium comprising water containing a mineral acid such as hydrochloric acid, sulfuric acid, nitric acid, etc., in the presence of a catalyst containing Pd, Pt and Rh at molar ratios of 1:1:1, at a relatively low temperature from normal temperature to 60°C under a hydrogen pressure of 1W10 atm for about several W10hr, to effect the aminomethylation of the raw material and the reduction of the benzene nucleus, thereby giving 4-aminomethylcyclohexanecarboxylic acid and its mineral acid salt. The above mineral acid selected is from those forming a water-soluble salt with the product.
USE: An intermediate for the preparation of trans-4-aminomethylcyclohexanecarboxylic acid useful as a medicine having anti-plasminic activity.
COPYRIGHT: (C)1982,JPO&Japio
JP55128962A 1980-09-17 1980-09-17 Method for producing 4-aminomethylcyclohexanecarboxylic acid and its mineral acid salt Expired JPS5951934B2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP55128962A JPS5951934B2 (en) 1980-09-17 1980-09-17 Method for producing 4-aminomethylcyclohexanecarboxylic acid and its mineral acid salt
CA000385915A CA1179369A (en) 1980-09-17 1981-09-15 Process for preparing 4-aminomethylcyclohexane-carboxylic acid or mineral acid salt thereof
FR8117501A FR2490218A1 (en) 1980-09-17 1981-09-16 PROCESS FOR THE PREPARATION OF 4-AMINOMETHYLCYCLOHEXANECARBOXYLIC ACID AND ITS SALTS WITH MINERAL ACIDS
GB8128010A GB2084145B (en) 1980-09-17 1981-09-16 Process for preparing 4-aminomethycyclohexane-carboxylic acid or mineral acid salt thereof
DE3137092A DE3137092C2 (en) 1980-09-17 1981-09-17 Process for the preparation of mixtures of cis- and trans-4-aminomethyl-cyclohexanecarboxylic acid in the form of the salts with certain mineral acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP55128962A JPS5951934B2 (en) 1980-09-17 1980-09-17 Method for producing 4-aminomethylcyclohexanecarboxylic acid and its mineral acid salt

Publications (2)

Publication Number Publication Date
JPS5753440A true JPS5753440A (en) 1982-03-30
JPS5951934B2 JPS5951934B2 (en) 1984-12-17

Family

ID=14997713

Family Applications (1)

Application Number Title Priority Date Filing Date
JP55128962A Expired JPS5951934B2 (en) 1980-09-17 1980-09-17 Method for producing 4-aminomethylcyclohexanecarboxylic acid and its mineral acid salt

Country Status (5)

Country Link
JP (1) JPS5951934B2 (en)
CA (1) CA1179369A (en)
DE (1) DE3137092C2 (en)
FR (1) FR2490218A1 (en)
GB (1) GB2084145B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010010869A1 (en) * 2008-07-23 2010-01-28 三菱瓦斯化学株式会社 Process for producing hydrogenated aromatic polycarboxylic acid
WO2021107047A1 (en) * 2019-11-29 2021-06-03 株式会社Ｄｎｐファインケミカル Method for producing 4-(aminomethyl)cyclohexane carboxylic acid

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102276490B (en) * 2011-06-30 2014-03-19 常州寅盛药业有限公司 Method for preparing tranexamic acid from para-aminomethylbenzoic acid by catalytic hydrogenation
CN113042040B (en) * 2021-03-26 2023-07-28 白云山东泰商丘药业有限公司 Method for preparing tranexamic acid by using platinum-carbon catalyst

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2265725A1 (en) * 1974-03-27 1975-10-24 Asahi Chemical Ind 4-Aminomethyl-cyclohexane carboxylic acid prepn. - by hydrogenating para-aminomethyl benzoic acid in presence of ruthenium catalysts and alkal-ine hydroxides
JPS5152159A (en) * 1974-10-31 1976-05-08 Toray Industries 44 asechiruaminomechirushikurohekisankarubonsan mataha sonojudotaino seizoho

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010010869A1 (en) * 2008-07-23 2010-01-28 三菱瓦斯化学株式会社 Process for producing hydrogenated aromatic polycarboxylic acid
US8846973B2 (en) 2008-07-23 2014-09-30 Mitsubishi Gas Chemical Company, Inc. Process for producing hydrogenated aromatic polycarboxylic acid
WO2021107047A1 (en) * 2019-11-29 2021-06-03 株式会社Ｄｎｐファインケミカル Method for producing 4-(aminomethyl)cyclohexane carboxylic acid

Also Published As

Publication number Publication date
GB2084145B (en) 1984-07-11
CA1179369A (en) 1984-12-11
FR2490218A1 (en) 1982-03-19
DE3137092C2 (en) 1983-02-03
FR2490218B1 (en) 1984-04-20
DE3137092A1 (en) 1982-04-08
JPS5951934B2 (en) 1984-12-17
GB2084145A (en) 1982-04-07

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