ES234060A1 - A procedure for obtaining hydrogenated amides of N-alkyl-alkyl-poteridine monocarboxylic acids (Machine-translation by Google Translate, not legally binding) - Google Patents
A procedure for obtaining hydrogenated amides of N-alkyl-alkyl-poteridine monocarboxylic acids (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES234060A1 ES234060A1 ES0234060A ES234060A ES234060A1 ES 234060 A1 ES234060 A1 ES 234060A1 ES 0234060 A ES0234060 A ES 0234060A ES 234060 A ES234060 A ES 234060A ES 234060 A1 ES234060 A1 ES 234060A1
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- monocarboxylic
- alkyl group
- acid
- amides
- 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
- 150000001408 amides Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 150000002763 monocarboxylic acids Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000003849 aromatic solvent Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A process for obtaining hydrogenated amides of N-alkyl-alkyl-piperidin monocarboxylic acid and N-alkyl-alkyl-pyrrolidin monocarboxylic acid, according to the formulas ** (See formula) ** wherein R1 designates an alkyl group, R2 and R3, either an alkyl group each or an alkyl group and the other a hydrogen atom, and in which Ar consists of a substituted benzene nucleus in which the substitution preferably consists of alkyl or alkoxy groups, characterized in that an alkyl magnesium halide of the formula: ** (See formula) ** wherein X denotes the halide and R4, R5 and R6 are substituents, such as a hydrogen atom, an alkyl group, a chlorine atom or an alkoxy group, is reacted with an ester, hydrogenated or not, of N-acid -alkyl pyrrolidine monocarboxylic or N-alkyl piperidine monocarboxylic which is or is not alkylated to the ring nitrogen, the mixture being maintained under reflux under continuous stirring, then cooling. The product of the reaction is then hydrolysed with an acid, whereby the impurities formed of magnesium are dissolved and hydrolyzed. The pH is adjusted to a value below 7, the aqueous base is separated and the excess that has not reacted with the ester is extracted with an aromatic solvent. The product formed is obtained by extracting it with a solvent liquid of the amide, after adding an excess of ammonia to the aqueous solution. The isoamyl alcohol solution is evaporated to dryness, the product is then dissolved in dilute hydrochloride, treated with activated carbon and finally precipitated with sodium hydroxide. Only the catalytic hydrogenation of the heterocyclic ring is carried out, and the alkylation of the ring nitrogen when this is the case. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE170156 | 1956-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES234060A1 true ES234060A1 (en) | 1957-11-01 |
Family
ID=38526955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0234060A Expired ES234060A1 (en) | 1956-02-22 | 1957-02-22 | A procedure for obtaining hydrogenated amides of N-alkyl-alkyl-poteridine monocarboxylic acids (Machine-translation by Google Translate, not legally binding) |
Country Status (7)
| Country | Link |
|---|---|
| BE (2) | BE554777A (en) |
| DE (2) | DE1228613B (en) |
| DK (3) | DK88970C (en) |
| ES (1) | ES234060A1 (en) |
| FR (1) | FR1225621A (en) |
| GB (1) | GB799778A (en) |
| NL (1) | NL98233C (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3138614A (en) * | 1961-12-18 | 1964-06-23 | Lilly Co Eli | Salts of 1, 1-dimethyl-3-pyrrolidyl phenyl-2-thienylglycolate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT180259B (en) * | 1952-02-25 | 1954-11-25 | Cilag Ag | Process for the preparation of new basic substituted fatty acid-2-halogen-6-methylanilides and their salts |
-
1957
- 1957-02-06 BE BE554777A patent/BE554777A/en unknown
- 1957-02-08 BE BE554837A patent/BE554837A/en unknown
- 1957-02-11 GB GB4583/57A patent/GB799778A/en not_active Expired
- 1957-02-14 DE DEA26583A patent/DE1228613B/en active Pending
- 1957-02-14 DE DEA26584A patent/DE1229091B/en active Pending
- 1957-02-18 FR FR732024A patent/FR1225621A/en not_active Expired
- 1957-02-21 DK DK65157AA patent/DK88970C/en active
- 1957-02-21 DK DK65057AA patent/DK87391C/en active
- 1957-02-21 NL NL214800A patent/NL98233C/en active
- 1957-02-21 DK DK65257AA patent/DK86988C/en active
- 1957-02-22 ES ES0234060A patent/ES234060A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL98233C (en) | 1961-06-15 |
| FR1225621A (en) | 1960-07-01 |
| DK86988C (en) | 1959-03-09 |
| GB799778A (en) | 1958-08-13 |
| DE1228613B (en) | 1966-11-17 |
| BE554777A (en) | 1960-01-29 |
| BE554837A (en) | 1960-02-12 |
| DK87391C (en) | 1959-06-08 |
| DK88970C (en) | 1960-05-16 |
| DE1229091B (en) | 1966-11-24 |
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