CA1052817A - Method for the production of trans-4-aminomethyl cyclohexane-1-carboxylic acid - Google Patents
Method for the production of trans-4-aminomethyl cyclohexane-1-carboxylic acidInfo
- Publication number
- CA1052817A CA1052817A CA253,330A CA253330A CA1052817A CA 1052817 A CA1052817 A CA 1052817A CA 253330 A CA253330 A CA 253330A CA 1052817 A CA1052817 A CA 1052817A
- Authority
- CA
- Canada
- Prior art keywords
- trans
- amcha
- cis
- carboxylic acid
- hydrochloride
- 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
- GYDJEQRTZSCIOI-UHFFFAOYSA-N Tranexamic acid Chemical compound NCC1CCC(C(O)=O)CC1 GYDJEQRTZSCIOI-UHFFFAOYSA-N 0.000 title claims abstract description 86
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 239000007789 gas Substances 0.000 claims abstract description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 11
- UGECKKSVDQIZQG-MEZFUOHNSA-N Cl.NC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound Cl.NC[C@H]1CC[C@H](C(O)=O)CC1 UGECKKSVDQIZQG-MEZFUOHNSA-N 0.000 claims abstract description 6
- UGECKKSVDQIZQG-UHFFFAOYSA-N 4-(aminomethyl)cyclohexane-1-carboxylic acid;hydron;chloride Chemical compound Cl.NCC1CCC(C(O)=O)CC1 UGECKKSVDQIZQG-UHFFFAOYSA-N 0.000 claims abstract 5
- 238000002844 melting Methods 0.000 claims description 16
- 230000008018 melting Effects 0.000 claims description 16
- 238000006317 isomerization reaction Methods 0.000 abstract description 12
- 238000010438 heat treatment Methods 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 6
- 238000000926 separation method Methods 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000000126 substance Substances 0.000 abstract 1
- 239000000306 component Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 239000003708 ampul Substances 0.000 description 8
- 238000007796 conventional method Methods 0.000 description 7
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 7
- 239000011521 glass Substances 0.000 description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 229920001429 chelating resin Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- -1 paratoluene sulfonates Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007038 hydrochlorination reaction Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 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
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical class [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical class [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical class OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229940071103 sulfosalicylate Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
Classifications
-
- 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
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/28—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50062452A JPS51138651A (en) | 1975-05-27 | 1975-05-27 | Process for pr eparing trans-4-aminomethyo-cyclohexane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052817A true CA1052817A (en) | 1979-04-17 |
Family
ID=13200600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA253,330A Expired CA1052817A (en) | 1975-05-27 | 1976-05-26 | Method for the production of trans-4-aminomethyl cyclohexane-1-carboxylic acid |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4071553A (enExample) |
| JP (1) | JPS51138651A (enExample) |
| CA (1) | CA1052817A (enExample) |
| DE (1) | DE2623130C3 (enExample) |
| FR (1) | FR2312488A1 (enExample) |
| GB (1) | GB1500224A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080022203A (ko) * | 2005-06-20 | 2008-03-10 | 제노포트 인코포레이티드 | 트라넥삼산의 아실옥시알킬 카르바메이트 프로드러그, 합성방법 및 용도 |
| WO2011028234A1 (en) * | 2009-09-04 | 2011-03-10 | Xenoport, Inc. | Uses of acyloxyalkyl carbamate prodrugs of tranexamic acid |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4727506U (enExample) * | 1971-04-19 | 1972-11-28 | ||
| JPS5129470A (en) * | 1974-09-03 | 1976-03-12 | Kureha Chemical Ind Co Ltd | Toransu 44 aminomechirushikurohekisan 11 karubonsan no seiho |
-
1975
- 1975-05-27 JP JP50062452A patent/JPS51138651A/ja active Granted
-
1976
- 1976-05-22 DE DE2623130A patent/DE2623130C3/de not_active Expired
- 1976-05-26 CA CA253,330A patent/CA1052817A/en not_active Expired
- 1976-05-26 FR FR7616077A patent/FR2312488A1/fr active Granted
- 1976-05-27 US US05/690,516 patent/US4071553A/en not_active Expired - Lifetime
- 1976-05-27 GB GB22096/76A patent/GB1500224A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS541297B2 (enExample) | 1979-01-23 |
| FR2312488A1 (fr) | 1976-12-24 |
| DE2623130A1 (de) | 1977-01-20 |
| GB1500224A (en) | 1978-02-08 |
| DE2623130B2 (de) | 1978-02-09 |
| FR2312488B1 (enExample) | 1981-02-13 |
| DE2623130C3 (de) | 1978-10-12 |
| US4071553A (en) | 1978-01-31 |
| JPS51138651A (en) | 1976-11-30 |
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