DE2038208A1 - Verfahren zur Herstellung des Trans-Isomeren von 4-Aminomethylcyclohexan-1-carbonsaeure - Google Patents
Verfahren zur Herstellung des Trans-Isomeren von 4-Aminomethylcyclohexan-1-carbonsaeureInfo
- Publication number
- DE2038208A1 DE2038208A1 DE19702038208 DE2038208A DE2038208A1 DE 2038208 A1 DE2038208 A1 DE 2038208A1 DE 19702038208 DE19702038208 DE 19702038208 DE 2038208 A DE2038208 A DE 2038208A DE 2038208 A1 DE2038208 A1 DE 2038208A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- isomer
- trans isomer
- aminomethylcyclohexane
- trans
- 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
Links
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 17
- GYDJEQRTZSCIOI-UHFFFAOYSA-N Tranexamic acid Chemical compound NCC1CCC(C(O)=O)CC1 GYDJEQRTZSCIOI-UHFFFAOYSA-N 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- 230000007062 hydrolysis Effects 0.000 claims description 13
- 238000006460 hydrolysis reaction Methods 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 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 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000003456 ion exchange resin Substances 0.000 claims description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 1
- 239000003708 ampul Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- UAFHRUBCOQPFFM-UHFFFAOYSA-N 1-(aminomethyl)cyclohexane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CCCCC1 UAFHRUBCOQPFFM-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 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
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5996569 | 1969-07-31 | ||
| JP5996569 | 1969-07-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2038208A1 true DE2038208A1 (de) | 1971-02-18 |
| DE2038208C DE2038208C (enExample) | 1973-02-08 |
Family
ID=13128374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702038208 Granted DE2038208A1 (de) | 1969-07-31 | 1970-07-31 | Verfahren zur Herstellung des Trans-Isomeren von 4-Aminomethylcyclohexan-1-carbonsaeure |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3711537A (enExample) |
| CH (1) | CH535741A (enExample) |
| DE (1) | DE2038208A1 (enExample) |
| GB (1) | GB1257406A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4665225A (en) * | 1985-09-12 | 1987-05-12 | Union Camp Corporation | Cycloaliphatic amino carboxylic acid |
| CN113677740A (zh) | 2019-04-03 | 2021-11-19 | 索尔维特殊聚合物美国有限责任公司 | 聚酰胺和对应的聚合物组合物及制品 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2790788A (en) * | 1952-12-23 | 1957-04-30 | Nat Distillers Prod Corp | Linear polyamide polymers of 4-aminocyclohexyl-acetic acid |
-
1970
- 1970-07-31 GB GB1257406D patent/GB1257406A/en not_active Expired
- 1970-07-31 DE DE19702038208 patent/DE2038208A1/de active Granted
- 1970-07-31 US US00060138A patent/US3711537A/en not_active Expired - Lifetime
- 1970-07-31 CH CH1163070A patent/CH535741A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US3711537A (en) | 1973-01-16 |
| GB1257406A (enExample) | 1971-12-15 |
| CH535741A (de) | 1973-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |