CA1186332A - Process for the preparation of carnitine chloride - Google Patents
Process for the preparation of carnitine chlorideInfo
- Publication number
- CA1186332A CA1186332A CA000406463A CA406463A CA1186332A CA 1186332 A CA1186332 A CA 1186332A CA 000406463 A CA000406463 A CA 000406463A CA 406463 A CA406463 A CA 406463A CA 1186332 A CA1186332 A CA 1186332A
- Authority
- CA
- Canada
- Prior art keywords
- carnitine
- chloride
- hours
- acid
- acid chloride
- 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 6
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 title abstract description 8
- 229960000678 carnitine chloride Drugs 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 229960004203 carnitine Drugs 0.000 claims abstract description 26
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 claims abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 13
- 239000012320 chlorinating reagent Substances 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 7
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
- GUYHPGUANSLONG-SNAWJCMRSA-N (E)-4-(trimethylammonio)but-2-enoate Chemical compound C[N+](C)(C)C\C=C\C([O-])=O GUYHPGUANSLONG-SNAWJCMRSA-N 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 239000006227 byproduct Substances 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 238000005755 formation reaction Methods 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910017974 NH40H Inorganic materials 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910006124 SOCl2 Inorganic materials 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- -1 esters and amides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JXXCENBLGFBQJM-UHFFFAOYSA-N (3-carboxy-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CC(O)=O JXXCENBLGFBQJM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy 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
-
- 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
- C07C227/18—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 involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- 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
- C07C229/04—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 acyclic and saturated
- C07C229/22—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 acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/115—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT48817A/81 | 1981-07-03 | ||
| IT48817/81A IT1171360B (it) | 1981-07-03 | 1981-07-03 | Procedimento per la preparazione del cloruro acido di carnitina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1186332A true CA1186332A (en) | 1985-04-30 |
Family
ID=11268676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000406463A Expired CA1186332A (en) | 1981-07-03 | 1982-06-30 | Process for the preparation of carnitine chloride |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5815943A (el) |
| KR (1) | KR860001886B1 (el) |
| AT (1) | AT390057B (el) |
| BE (1) | BE893713A (el) |
| CA (1) | CA1186332A (el) |
| CH (1) | CH648546A5 (el) |
| DE (1) | DE3224666A1 (el) |
| DK (1) | DK154425C (el) |
| ES (1) | ES513658A0 (el) |
| FR (1) | FR2510559B1 (el) |
| GB (1) | GB2101133B (el) |
| GR (1) | GR76546B (el) |
| IE (1) | IE53279B1 (el) |
| IL (1) | IL66251A0 (el) |
| IT (1) | IT1171360B (el) |
| LU (1) | LU84244A1 (el) |
| NL (1) | NL189666C (el) |
| SE (1) | SE448724B (el) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190358B (it) * | 1985-05-24 | 1988-02-16 | Sclavo Spa | Procedimento per la preparazione di l-carnitina |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3940439A (en) * | 1973-11-14 | 1976-02-24 | G. D. Searle & Co. | Acid chloride synthesis |
| IT1116037B (it) * | 1979-04-23 | 1986-02-10 | Sigma Tau Ind Farmaceuti | Esteri e ammidi di acil carnitine loro procedimenti di preparazione e loro uso terapeutico |
| DE2943433A1 (de) * | 1979-10-26 | 1981-05-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von carbonsaeurehalogeniden |
-
1981
- 1981-07-03 IT IT48817/81A patent/IT1171360B/it active
-
1982
- 1982-06-24 CH CH3884/82A patent/CH648546A5/it not_active IP Right Cessation
- 1982-06-25 IE IE1524/82A patent/IE53279B1/en not_active IP Right Cessation
- 1982-06-29 GB GB08218824A patent/GB2101133B/en not_active Expired
- 1982-06-30 BE BE0/208502A patent/BE893713A/fr not_active IP Right Cessation
- 1982-06-30 DK DK295482A patent/DK154425C/da not_active IP Right Cessation
- 1982-06-30 CA CA000406463A patent/CA1186332A/en not_active Expired
- 1982-06-30 LU LU84244A patent/LU84244A1/fr unknown
- 1982-07-01 DE DE19823224666 patent/DE3224666A1/de active Granted
- 1982-07-01 KR KR8202945A patent/KR860001886B1/ko active
- 1982-07-01 GR GR68615A patent/GR76546B/el unknown
- 1982-07-02 SE SE8204117A patent/SE448724B/sv not_active IP Right Cessation
- 1982-07-02 FR FR8211685A patent/FR2510559B1/fr not_active Expired
- 1982-07-02 NL NLAANVRAGE8202677,A patent/NL189666C/xx not_active IP Right Cessation
- 1982-07-02 JP JP57116084A patent/JPS5815943A/ja active Granted
- 1982-07-02 AT AT0257382A patent/AT390057B/de not_active IP Right Cessation
- 1982-07-02 ES ES513658A patent/ES513658A0/es active Granted
- 1982-07-07 IL IL66251A patent/IL66251A0/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL66251A0 (en) | 1982-11-30 |
| NL8202677A (nl) | 1983-02-01 |
| ES8304064A1 (es) | 1983-03-01 |
| DK154425B (da) | 1988-11-14 |
| DK295482A (da) | 1983-01-04 |
| IE821524L (en) | 1983-01-03 |
| NL189666B (nl) | 1993-01-18 |
| NL189666C (nl) | 1993-06-16 |
| BE893713A (fr) | 1982-10-18 |
| GB2101133B (en) | 1985-08-14 |
| KR840000475A (ko) | 1984-02-22 |
| JPS5815943A (ja) | 1983-01-29 |
| ATA257382A (de) | 1989-08-15 |
| SE8204117L (sv) | 1983-01-04 |
| SE8204117D0 (sv) | 1982-07-02 |
| KR860001886B1 (ko) | 1986-10-24 |
| DE3224666C2 (el) | 1991-01-24 |
| ES513658A0 (es) | 1983-03-01 |
| CH648546A5 (it) | 1985-03-29 |
| GB2101133A (en) | 1983-01-12 |
| AT390057B (de) | 1990-03-12 |
| IT1171360B (it) | 1987-06-10 |
| LU84244A1 (fr) | 1983-01-20 |
| FR2510559B1 (fr) | 1986-05-09 |
| DE3224666A1 (de) | 1983-01-20 |
| GR76546B (el) | 1984-08-10 |
| SE448724B (sv) | 1987-03-16 |
| JPH0244300B2 (el) | 1990-10-03 |
| FR2510559A1 (fr) | 1983-02-04 |
| IT8148817A0 (it) | 1981-07-03 |
| DK154425C (da) | 1989-04-10 |
| IE53279B1 (en) | 1988-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |