CS392291A3 - Process for preparing procaine - Google Patents
Process for preparing procaineInfo
- Publication number
- CS392291A3 CS392291A3 CS913922A CS392291A CS392291A3 CS 392291 A3 CS392291 A3 CS 392291A3 CS 913922 A CS913922 A CS 913922A CS 392291 A CS392291 A CS 392291A CS 392291 A3 CS392291 A3 CS 392291A3
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- procaine
- preparing
- alcohol
- diethylaminoethanol
- esterified
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 title 1
- 229960004919 procaine Drugs 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- -1 nitro ester Chemical class 0.000 abstract 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 abstract 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
Classifications
-
- 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
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compounds Of Unknown Constitution (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The process is characterised in that p-nitrobenzoic acid is esterified in butanol in a manner known per se, the nitro ester is catalytically hydrogenated without intermediate isolation and the resulting hydrogenation solution, after removal by distillation of the majority of the alcohol used, is reacted with diethylaminoethanol in the presence of alkali metal alkoxides at 80 to 150 DEG C, preferably 80 to 130 DEG C, and in the course of this the alcohol liberated is continuously removed in vacuo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4041179A DE4041179A1 (en) | 1990-12-21 | 1990-12-21 | PROCESS FOR PRODUCING PROCAIN |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS392291A3 true CS392291A3 (en) | 1992-07-15 |
| CZ282438B6 CZ282438B6 (en) | 1997-07-16 |
Family
ID=6421030
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0492494B1 (en) |
| JP (1) | JPH04295452A (en) |
| CN (1) | CN1028360C (en) |
| AT (1) | ATE140915T1 (en) |
| CZ (1) | CZ282438B6 (en) |
| DE (3) | DE4042433A1 (en) |
| DK (1) | DK0492494T3 (en) |
| ES (1) | ES2091855T3 (en) |
| GR (1) | GR3020704T3 (en) |
| HU (1) | HU208303B (en) |
| MX (1) | MX9102747A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118420476A (en) * | 2023-02-01 | 2024-08-02 | 重庆康丁医药技术有限公司 | A green synthesis method of procaine hydrochloride |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1396913A (en) * | 1917-10-11 | 1921-11-15 | Levinstein Ltd | Production of aminoalkylesters and of alkylaminoalkylesters of para aminobenzoic acid |
| US1676470A (en) * | 1921-09-27 | 1928-07-10 | Abbott Lab | Production of esters of aromatic acids |
| AT213874B (en) * | 1958-08-22 | 1961-03-10 | Leuna Werke Veb | Process for the preparation of p-aminobenzoic acid alkamine esters |
| US3660411A (en) * | 1970-06-15 | 1972-05-02 | Universal Oil Prod Co | Esterification process |
-
1990
- 1990-12-21 DE DE4042433A patent/DE4042433A1/en not_active Withdrawn
- 1990-12-21 DE DE4041179A patent/DE4041179A1/en not_active Withdrawn
-
1991
- 1991-12-19 CZ CS913922A patent/CZ282438B6/en unknown
- 1991-12-20 DE DE59108052T patent/DE59108052D1/en not_active Expired - Fee Related
- 1991-12-20 ES ES91121929T patent/ES2091855T3/en not_active Expired - Lifetime
- 1991-12-20 JP JP3337432A patent/JPH04295452A/en active Pending
- 1991-12-20 MX MX9102747A patent/MX9102747A/en not_active IP Right Cessation
- 1991-12-20 EP EP91121929A patent/EP0492494B1/en not_active Expired - Lifetime
- 1991-12-20 CN CN91111746.6A patent/CN1028360C/en not_active Expired - Fee Related
- 1991-12-20 DK DK91121929.3T patent/DK0492494T3/en active
- 1991-12-20 AT AT91121929T patent/ATE140915T1/en not_active IP Right Cessation
- 1991-12-20 HU HU914076A patent/HU208303B/en not_active IP Right Cessation
-
1996
- 1996-08-01 GR GR960402049T patent/GR3020704T3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0492494B1 (en) | 1996-07-31 |
| HU208303B (en) | 1993-09-28 |
| CN1028360C (en) | 1995-05-10 |
| CZ282438B6 (en) | 1997-07-16 |
| ATE140915T1 (en) | 1996-08-15 |
| DE4042433A1 (en) | 1992-09-03 |
| DE4041179A1 (en) | 1992-07-02 |
| ES2091855T3 (en) | 1996-11-16 |
| JPH04295452A (en) | 1992-10-20 |
| DK0492494T3 (en) | 1996-12-02 |
| CN1062722A (en) | 1992-07-15 |
| MX9102747A (en) | 1992-06-01 |
| HU914076D0 (en) | 1992-03-30 |
| DE59108052D1 (en) | 1996-09-05 |
| HUT59657A (en) | 1992-06-29 |
| EP0492494A1 (en) | 1992-07-01 |
| GR3020704T3 (en) | 1996-11-30 |
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