DE1543847A1 - d,I-,l- und d-Carnitinamidchloriden und ein Verfahren zu deren Herstellung - Google Patents
d,I-,l- und d-Carnitinamidchloriden und ein Verfahren zu deren HerstellungInfo
- Publication number
- DE1543847A1 DE1543847A1 DE19661543847 DE1543847A DE1543847A1 DE 1543847 A1 DE1543847 A1 DE 1543847A1 DE 19661543847 DE19661543847 DE 19661543847 DE 1543847 A DE1543847 A DE 1543847A DE 1543847 A1 DE1543847 A1 DE 1543847A1
- Authority
- DE
- Germany
- Prior art keywords
- chloride
- carnitine
- solution
- amide
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 20
- PHIQHXFUZVPYII-LURJTMIESA-N (S)-carnitine Chemical compound C[N+](C)(C)C[C@@H](O)CC([O-])=O PHIQHXFUZVPYII-LURJTMIESA-N 0.000 title claims description 7
- 150000001805 chlorine compounds Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 229960004203 carnitine Drugs 0.000 claims description 3
- -1 carnitine nitrile Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- UKHWJBVVWVYFEY-UHFFFAOYSA-M silver;hydroxide Chemical compound [OH-].[Ag+] UKHWJBVVWVYFEY-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZOYKKWXSDFNANU-UHFFFAOYSA-M (3-cyano-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CC#N ZOYKKWXSDFNANU-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- ZOYKKWXSDFNANU-OGFXRTJISA-M [(2r)-3-cyano-2-hydroxypropyl]-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)C[C@H](O)CC#N ZOYKKWXSDFNANU-OGFXRTJISA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
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 |
|---|---|---|---|
| BE659194A BE659194A (enrdf_load_stackoverflow) | 1965-02-03 | 1965-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1543847A1 true DE1543847A1 (de) | 1970-07-02 |
Family
ID=3847253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543847 Pending DE1543847A1 (de) | 1965-02-03 | 1966-01-31 | d,I-,l- und d-Carnitinamidchloriden und ein Verfahren zu deren Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE659194A (enrdf_load_stackoverflow) |
| CH (1) | CH447209A (enrdf_load_stackoverflow) |
| DE (1) | DE1543847A1 (enrdf_load_stackoverflow) |
| ES (1) | ES322595A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1464344A (enrdf_load_stackoverflow) |
| GB (1) | GB1075562A (enrdf_load_stackoverflow) |
| NL (1) | NL6600739A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2096103A4 (en) * | 2006-11-09 | 2012-11-21 | Mitsubishi Rayon Co | PROCESS FOR PREPARING A BETAIN |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1156852B (it) * | 1978-07-10 | 1987-02-04 | Sigma Tau Ind Farmaceuti | Procedimento industriale per la preparazione del d'canforato della l carnitinammide e del d canforato della d carnitinammide e sue applicazioni |
| CN101304965A (zh) | 2005-09-28 | 2008-11-12 | 三菱瓦斯化学株式会社 | 制备肉碱酰胺的方法 |
| EP1852416A1 (en) * | 2006-05-04 | 2007-11-07 | Universita'degli Studi Di Milano | Enantiomeric resolution of a carnitinamide salt by preferential crystallization |
-
1965
- 1965-02-03 BE BE659194A patent/BE659194A/xx unknown
-
1966
- 1966-01-12 FR FR45609A patent/FR1464344A/fr not_active Expired
- 1966-01-20 NL NL6600739A patent/NL6600739A/xx unknown
- 1966-01-31 DE DE19661543847 patent/DE1543847A1/de active Pending
- 1966-02-02 GB GB468566A patent/GB1075562A/en not_active Expired
- 1966-02-03 CH CH150666A patent/CH447209A/fr unknown
- 1966-02-03 ES ES0322595A patent/ES322595A1/es not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2096103A4 (en) * | 2006-11-09 | 2012-11-21 | Mitsubishi Rayon Co | PROCESS FOR PREPARING A BETAIN |
| US8334132B2 (en) | 2006-11-09 | 2012-12-18 | Mitsubishi Rayon Co., Ltd. | Process for production of a betaine such as carnitine |
Also Published As
| Publication number | Publication date |
|---|---|
| BE659194A (enrdf_load_stackoverflow) | 1965-08-03 |
| GB1075562A (en) | 1967-07-12 |
| FR1464344A (fr) | 1966-12-30 |
| NL6600739A (enrdf_load_stackoverflow) | 1966-08-04 |
| CH447209A (fr) | 1967-11-30 |
| ES322595A1 (es) | 1966-11-16 |
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