DE2623130C3 - Verfahren zur Herstellung von trans^-Aminomethyl-cyclohexan-l -carbonsäure durch Isomerisierung - Google Patents
Verfahren zur Herstellung von trans^-Aminomethyl-cyclohexan-l -carbonsäure durch IsomerisierungInfo
- Publication number
- DE2623130C3 DE2623130C3 DE2623130A DE2623130A DE2623130C3 DE 2623130 C3 DE2623130 C3 DE 2623130C3 DE 2623130 A DE2623130 A DE 2623130A DE 2623130 A DE2623130 A DE 2623130A DE 2623130 C3 DE2623130 C3 DE 2623130C3
- Authority
- DE
- Germany
- Prior art keywords
- trans
- amchs
- cis
- hydrochloride
- aminomethyl
- 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
- 238000000034 method Methods 0.000 title claims description 18
- 238000006317 isomerization reaction Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 7
- GYDJEQRTZSCIOI-UHFFFAOYSA-N Tranexamic acid Chemical compound NCC1CCC(C(O)=O)CC1 GYDJEQRTZSCIOI-UHFFFAOYSA-N 0.000 claims description 6
- 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 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- 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 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000003708 ampul Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000243 solution Substances 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
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000006228 supernatant Substances 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
- QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 description 1
- 229960003375 aminomethylbenzoic acid Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000001567 anti-fibrinolytic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005984 hydrogenation 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
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 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 (3)
| Publication Number | Publication Date |
|---|---|
| DE2623130A1 DE2623130A1 (de) | 1977-01-20 |
| DE2623130B2 DE2623130B2 (de) | 1978-02-09 |
| DE2623130C3 true DE2623130C3 (de) | 1978-10-12 |
Family
ID=13200600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2623130A Expired DE2623130C3 (de) | 1975-05-27 | 1976-05-22 | Verfahren zur Herstellung von trans^-Aminomethyl-cyclohexan-l -carbonsäure durch Isomerisierung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4071553A (show.php) |
| JP (1) | JPS51138651A (show.php) |
| CA (1) | CA1052817A (show.php) |
| DE (1) | DE2623130C3 (show.php) |
| FR (1) | FR2312488A1 (show.php) |
| GB (1) | GB1500224A (show.php) |
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 (show.php) * | 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 (show.php) | 1979-01-23 |
| FR2312488A1 (fr) | 1976-12-24 |
| DE2623130A1 (de) | 1977-01-20 |
| GB1500224A (en) | 1978-02-08 |
| DE2623130B2 (de) | 1978-02-09 |
| FR2312488B1 (show.php) | 1981-02-13 |
| CA1052817A (en) | 1979-04-17 |
| US4071553A (en) | 1978-01-31 |
| JPS51138651A (en) | 1976-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |