DE1228613B - Verfahren zur Herstellung von 2', 6'-disubstituierten N-Alkylpiperidin-2-monocarbonsaeureaniliden - Google Patents
Verfahren zur Herstellung von 2', 6'-disubstituierten N-Alkylpiperidin-2-monocarbonsaeureanilidenInfo
- Publication number
- DE1228613B DE1228613B DEA26583A DEA0026583A DE1228613B DE 1228613 B DE1228613 B DE 1228613B DE A26583 A DEA26583 A DE A26583A DE A0026583 A DEA0026583 A DE A0026583A DE 1228613 B DE1228613 B DE 1228613B
- Authority
- DE
- Germany
- Prior art keywords
- alkylpiperidine
- monocarboxylic acid
- disubstituted
- alkyl
- general formula
- 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
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 2-chloro-6-aminocaproic acid chloride hydrochloride Chemical compound 0.000 claims description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000003931 anilides Chemical class 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052801 chlorine Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 claims 1
- DDSZWBCJXDRQDU-UHFFFAOYSA-N [N].C1CCNCC1 Chemical group [N].C1CCNCC1 DDSZWBCJXDRQDU-UHFFFAOYSA-N 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 230000037005 anaesthesia Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 230000008595 infiltration Effects 0.000 description 3
- 238000001764 infiltration Methods 0.000 description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229940035674 anesthetics Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- OTHAXHPPJLNGHZ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-6-methylpiperidine-2-carboxamide Chemical compound N1C(C)CCCC1C(=O)NC1=C(C)C=CC=C1C OTHAXHPPJLNGHZ-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE170156 | 1956-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1228613B true DE1228613B (de) | 1966-11-17 |
Family
ID=38526955
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA26583A Pending DE1228613B (de) | 1956-02-22 | 1957-02-14 | Verfahren zur Herstellung von 2', 6'-disubstituierten N-Alkylpiperidin-2-monocarbonsaeureaniliden |
| DEA26584A Pending DE1229091B (de) | 1956-02-22 | 1957-02-14 | Verfahren zur Herstellung von 2', 6'-disubstituierten 1-Alkylpiperidin-2-monocarbonsaeureaniliden |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA26584A Pending DE1229091B (de) | 1956-02-22 | 1957-02-14 | Verfahren zur Herstellung von 2', 6'-disubstituierten 1-Alkylpiperidin-2-monocarbonsaeureaniliden |
Country Status (7)
| Country | Link |
|---|---|
| BE (2) | BE554777A (da) |
| DE (2) | DE1228613B (da) |
| DK (3) | DK88970C (da) |
| ES (1) | ES234060A1 (da) |
| FR (1) | FR1225621A (da) |
| GB (1) | GB799778A (da) |
| NL (1) | NL98233C (da) |
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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT180259B (de) * | 1952-02-25 | 1954-11-25 | Cilag Ag | Verfahren zur Herstellung von neuen basisch substituierten Fettsäure-2-halogen-6-methylaniliden und ihren Salzen |
-
1957
- 1957-02-06 BE BE554777A patent/BE554777A/fr unknown
- 1957-02-08 BE BE554837A patent/BE554837A/fr unknown
- 1957-02-11 GB GB4583/57A patent/GB799778A/en not_active Expired
- 1957-02-14 DE DEA26583A patent/DE1228613B/de active Pending
- 1957-02-14 DE DEA26584A patent/DE1229091B/de active Pending
- 1957-02-18 FR FR732024A patent/FR1225621A/fr not_active Expired
- 1957-02-21 DK DK65157AA patent/DK88970C/da active
- 1957-02-21 DK DK65257AA patent/DK86988C/da active
- 1957-02-21 DK DK65057AA patent/DK87391C/da active
- 1957-02-21 NL NL214800A patent/NL98233C/nl active
- 1957-02-22 ES ES0234060A patent/ES234060A1/es not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT180259B (de) * | 1952-02-25 | 1954-11-25 | Cilag Ag | Verfahren zur Herstellung von neuen basisch substituierten Fettsäure-2-halogen-6-methylaniliden und ihren Salzen |
Also Published As
| Publication number | Publication date |
|---|---|
| DK86988C (da) | 1959-03-09 |
| FR1225621A (fr) | 1960-07-01 |
| BE554777A (fr) | 1960-01-29 |
| DE1229091B (de) | 1966-11-24 |
| DK88970C (da) | 1960-05-16 |
| ES234060A1 (es) | 1957-11-01 |
| NL98233C (nl) | 1961-06-15 |
| GB799778A (en) | 1958-08-13 |
| BE554837A (fr) | 1960-02-12 |
| DK87391C (da) | 1959-06-08 |
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