GB824542A - Method of producing n-alkyl-piperidine-alpha-monocarboxylic acid amides - Google Patents
Method of producing n-alkyl-piperidine-alpha-monocarboxylic acid amidesInfo
- Publication number
- GB824542A GB824542A GB1236658A GB1236658A GB824542A GB 824542 A GB824542 A GB 824542A GB 1236658 A GB1236658 A GB 1236658A GB 1236658 A GB1236658 A GB 1236658A GB 824542 A GB824542 A GB 824542A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- alkyl
- alkyl group
- compounds
- bromide
- 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 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 239000012024 dehydrating agents Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 abstract 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 abstract 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000003931 anilides Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 abstract 1
- 229910003446 platinum oxide Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0824542/IV (b)/1> (wherein R is an alkyl group of at most 8 carbon atoms and Ar is a benzene ring containing an alkyl group of at most 3 carbon atoms in the 3 -or 4-position) and the preparation of these compounds and of compounds of the above general formula Ar may additionally represent a benzene ring substituted by an alkyl group at the 2-position or by alkyl groups at the 2:6- or 2:4:6-positions, the total number of carbon atoms in these alkyl substituents not exceeding 3, by treating the picolinic acid salt of NH2Ar with a dehydrating agent at above 85 DEG C., and preferably at 90 DEG to 140 DEG C., to form the corresponding picolyl anilide, then hydrogenating the pyridine ring and, lastly, alkylating the nuclear nitrogen atom. The dehydrating agent is advantageously a chlorine containing compound such as phosphorus oxychloride. The above process may be combined with the preparation of the picolinic acid salt by heating, e.g. at 125 DEG C., the acid with the amine in the presence of a tertiary base such as N-methylpyrrolidone. In examples, the hydrogenations are effected by hydrogen under pressure in the presence of glacial acetic acid and platinum oxide catalyst and the alkylations are effected with, variously, dimethyl sulphate, n-amyl bromide, n-octyl bromide, diethyl sulphate and n-butyl bromide. Specifications 770,129 and 772,807 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE462657 | 1957-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB824542A true GB824542A (en) | 1959-12-02 |
Family
ID=20264618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1236658A Expired GB824542A (en) | 1957-05-15 | 1958-04-18 | Method of producing n-alkyl-piperidine-alpha-monocarboxylic acid amides |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH369759A (en) |
| DE (1) | DE1292142B (en) |
| GB (1) | GB824542A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4695576A (en) * | 1984-07-09 | 1987-09-22 | Astra Lake Medel Aktiebolag | L-N-n-propylpipecolic acid-2,6-xylidide |
| US4870086A (en) * | 1986-01-03 | 1989-09-26 | Astra Lakemedel Aktiebolag | Optically pure compound and a process for its preparation |
| WO2009089842A1 (en) | 2008-01-15 | 2009-07-23 | Pharmathen S.A. | Process for producing pipecolic-2-acid-2 ',6'-xylidide useful as an intermediate for the preparation of local anesthetics |
| CN102558030A (en) * | 2010-12-11 | 2012-07-11 | 山东方明药业股份有限公司 | Synthesis of 1-N-(2,6-dimethyl phenyl)-2-piperidinecarboxamide |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE539965A (en) * | ||||
| BE539933A (en) * | ||||
| DE644839C (en) * | 1934-12-05 | 1937-05-14 | Chemische Ind Ges | Process for the preparation of pyridine-o-dicarboxylic acid amides |
| US2439728A (en) * | 1941-08-30 | 1948-04-13 | Du Pont | Pyridine carbonyl amides of the benzene series |
| US2792399A (en) * | 1954-05-29 | 1957-05-14 | Bofors Ab | Anilides of heterocyclic compounds |
| BE539896A (en) * | 1954-07-21 | 1959-07-17 | Bofors Ab | PROCEDURE FOR THE MANUFACTURE OF N-ALKYL-PIPERIDINE-MONOCARBOXYLIC AMIDES. |
| AT195429B (en) * | 1955-04-06 | 1958-02-10 | Bofors Ab | Process for the preparation of new heterocyclic monocarboxamides |
| AT190931B (en) * | 1955-04-28 | 1957-07-25 | Bofors Ab | Process for the preparation of new heterocyclic monocarboxamides |
-
1958
- 1958-04-18 GB GB1236658A patent/GB824542A/en not_active Expired
- 1958-04-21 CH CH5857558A patent/CH369759A/en unknown
- 1958-05-06 DE DEA29428A patent/DE1292142B/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4695576A (en) * | 1984-07-09 | 1987-09-22 | Astra Lake Medel Aktiebolag | L-N-n-propylpipecolic acid-2,6-xylidide |
| US4870086A (en) * | 1986-01-03 | 1989-09-26 | Astra Lakemedel Aktiebolag | Optically pure compound and a process for its preparation |
| WO2009089842A1 (en) | 2008-01-15 | 2009-07-23 | Pharmathen S.A. | Process for producing pipecolic-2-acid-2 ',6'-xylidide useful as an intermediate for the preparation of local anesthetics |
| CN102558030A (en) * | 2010-12-11 | 2012-07-11 | 山东方明药业股份有限公司 | Synthesis of 1-N-(2,6-dimethyl phenyl)-2-piperidinecarboxamide |
Also Published As
| Publication number | Publication date |
|---|---|
| CH369759A (en) | 1963-06-15 |
| DE1292142B (en) | 1969-04-10 |
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