GB772807A - Method for the preparation of n-alkyl piperidine monocarboxylic acid amides - Google Patents
Method for the preparation of n-alkyl piperidine monocarboxylic acid amidesInfo
- Publication number
- GB772807A GB772807A GB20715/55A GB2071555A GB772807A GB 772807 A GB772807 A GB 772807A GB 20715/55 A GB20715/55 A GB 20715/55A GB 2071555 A GB2071555 A GB 2071555A GB 772807 A GB772807 A GB 772807A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anilide
- dimethyl
- give
- ethyl
- methyl
- 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
- -1 pyridine compound Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 abstract 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 abstract 1
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 abstract 1
- WZIYCIBURCPKAR-UHFFFAOYSA-N 4-(chloromethyl)pyridine Chemical compound ClCC1=CC=NC=C1 WZIYCIBURCPKAR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical class NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Piperidine carboxylic acid amides of the formula <FORM:0772807/IV(b)/1> wherein R2 is alkyl, R2 is an alkyl group or not more than 5 carbon atoms or a chlorine atom, R3 is hydrogen, hydroxyl an alkyl group of not more than 5 carbon atoms or an alkoxy group, R4 is hydrogen, or chlorine, an alkyl group of not more than 5 carbon atoms, or an alkoxy group, or R2, R3 and R4 are all hydrogen are made by hydrogenating the corresponding pyridine compound (obtainable by reacting a pyridine monocarboxylic halide with the appropriate aromatic amine) and alkylating the nuclear nitrogen atom of the resulting piperidine compound. In examples: (1) picolinyl chloride is reacted with 2:6-dimethyl aniline, the resulting picolinyl dimethyl anilide is catalytically hydrogenated to pipecolinolyl-2:6-dimethyl anilide and this is alkylated with diethyl sulphate to give N-ethyl pipecolinyl-2:6-dimethyl anilide; (2) pipecolinyl-2:6-dimethyl anilide, made as in (1) is treated with dimethyl sulphate to give the corresponding N-methyl derivative; (3) nicotinyl chloride is reacted with 2-chloro-6-methyl-aniline, the resulting nicotinyl 2-chloro-6-methyl anilide is hydrogenated and the product is treated with diethyl sulphate to give N - ethyl nipecotinyl - 2 - chloro - 6 - methyl anilide and (4) isonicotinyl chloride is reacted with 2-ethyl aniline and the pro uct is hydrogenated to give isonipecotinyl-2-ethyl-anilide which is alkylated with n-butyl bromide to give N-n-butyl isonipecotinyl-2-ethyl anilide. Specification 770,129 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE772807X | 1954-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB772807A true GB772807A (en) | 1957-04-17 |
Family
ID=20333392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20715/55A Expired GB772807A (en) | 1954-07-21 | 1955-07-18 | Method for the preparation of n-alkyl piperidine monocarboxylic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB772807A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3544579A (en) * | 1967-03-09 | 1970-12-01 | Astra Ab | Substituted phenylcarbamic acid esters of cyclic amino alcohols |
| WO2009090173A1 (en) * | 2008-01-15 | 2009-07-23 | Neurosearch A/S | Novel piperidine-4-carboxylic acid phenyl-alkyl-amide derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
-
1955
- 1955-07-18 GB GB20715/55A patent/GB772807A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3544579A (en) * | 1967-03-09 | 1970-12-01 | Astra Ab | Substituted phenylcarbamic acid esters of cyclic amino alcohols |
| WO2009090173A1 (en) * | 2008-01-15 | 2009-07-23 | Neurosearch A/S | Novel piperidine-4-carboxylic acid phenyl-alkyl-amide derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
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