GB967177A - A method for preparing pyrrolidinones and piperidinones - Google Patents
A method for preparing pyrrolidinones and piperidinonesInfo
- Publication number
- GB967177A GB967177A GB3463260A GB3463260A GB967177A GB 967177 A GB967177 A GB 967177A GB 3463260 A GB3463260 A GB 3463260A GB 3463260 A GB3463260 A GB 3463260A GB 967177 A GB967177 A GB 967177A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- pyrrolidinone
- dimethyl
- piperidinone
- 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
Classifications
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Pyrrolidinones and piperidinones with, in the 5 and 6 positions respectively, a hydrogen atom and optionally a hydrocarbon group which may be joined to another carbon atom in the ring to form a cyclic group are prepared by reacting corresponding pyrrolidinones or piperidinones substituted in the 5 and 6 position respectively by a hydroxyl, alkoxyl, or an alkylamino group in which the alkyl group may be substituted by hydroxyl, aryl, or alkylamino groups and the optional second hydrocarbon substituent, with hydrogen in the presence of a hydrogenolysis catalyst. Lists of starting compounds are given, among them compounds of formula <FORM:0967177/C1/1> in which R represents hydrogen, an alkyl group (1-18C), an aryl group (up to 10C) an aralkyl group (up to 18C), an alkaryl group (up to 24C), an alkarylalkyl group (up to 30C), an alkoxyalkyl group (3 to 24C), hydroxyalkyl (2-12C), an alkylamino alkyl (3-18C), or a dialkylamino alkyl group (3-18C) in which the dialkyl substituents may be joined to form a cyclic group, R1 represents hydrocarbon groups (1-10C), R2 represents a hydroxyl, alkoxyl (1-4C) alkylamino (1-12C) which may be substituted by a hydroxyl, alkoxyl, aryl or alkylamino group, and D is a divalent chain containing 2 to 3C atoms which yield compounds of formula <FORM:0967177/C1/2> Catalysts for the hydrogenation are Raney nickel or cobalt, cobalt or nickel with ammonia, cobalt-copper, nickel-cobalt, palladium, platinum, rubidium and ruthenium with or without a carrier such as activated alumina or clays, silica gel, charcoal, asbestos and pumice. A solvent, such as hydrocarbons, alcohols and ethers may be present and the product is separated by filtration and stripping of the solvent. The starting materials may be obtained by the cyclisation of g - and d - oxonitriles followed by hydration with aqueous alkali. Examples describe the preparation of 3,3,5-trimethyl -2- pyrolidinone, 3,5-dimethyl -3- neopentyl -2- pyrrolidinone, 5,5-dimethyl -2- piperidinone, 4,5-dimethyl -2- pyrrolidinone, 1-benzyl-3, 3, 5-trimethyl -2- pyrrolidinone, 1-(2-phenylethyl)-3,3,6-trimethyl-2- piperidinone, 1-(2-hydroxy propyl)-5, 5-dimethyl -2- piperidinone, 1-(2-methyl aminoethyl)-3, 5-dimethyl -3- hexyl -2- pyrrolidinone spiro {3,3-dimethylbicyclo (2,2,1) heptane-2, 31-[51-methyl -21- pyrrloidinone]}, 1 -ptolyl-3, 3, 5-trimethyl -2- pyrrolidinone, 1-(2-hydroxy ethyl)-3, 5-bis-(2-methylpropyl)-3-methyl -2- pyrrolidinone, 1-(3-dimethyl-aminopropyl)-4, 6-dimethyl -4- neopentyl -2- piperidinone, 3, 3-pentamethylene-2, 3, 3a, 4, 5, 6, 7, 7a-octahydroindol -2- one, 3-methyl-1, 3, 3a, 4, 5, 6, 7, 7a-octahydroisoindol -1- one, 5, 6-dimethyl -2- piperidinone, 5-methyl -2- pyrrolidinone, 3, 3, 6-trimethyl-2, 3, 3a, 4, 5, 6, 7, 7a-octahydroindol-2-one, 6-oza -7- oxo 1, 3, 3-trimethylbicyclo (3, 2, 1) octane, 5-ethyl -5- butyl -2- piperidinone, 3, 5-dihexyl -3- methyl -2- pyrolidinone, 1, 3, 3, 5-tetramethyl -2- pyrrolidinone, 1, 3-dimethyl-3, 5-dihexyl -2- pyrrolidinone, 1-ethyl-3, 3, 6-tri, methyl -2- piperidinone and 1-dodecyl-3, 5, 5-trimethyl -2- piperidinone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84606959A | 1959-10-13 | 1959-10-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB967177A true GB967177A (en) | 1964-08-19 |
Family
ID=25296853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3463260A Expired GB967177A (en) | 1959-10-13 | 1960-10-10 | A method for preparing pyrrolidinones and piperidinones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB967177A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4473696A (en) * | 1982-10-07 | 1984-09-25 | Ici Americas Inc. | Synthesis of 2-substituted-5-methyl-pyridines |
| US4658031A (en) * | 1982-10-07 | 1987-04-14 | Ici Americas Inc. | Synthesis of 2-substituted-5-methyl-pyridines and intermediates therefor |
| US4687854A (en) * | 1982-10-07 | 1987-08-18 | Ici Americas Inc. | Bispiperidone precursor of 2-substituted-5-methyl-pyridines |
| TWI799435B (en) * | 2017-08-02 | 2023-04-21 | 美商維泰克斯製藥公司 | Processes for preparing compounds |
| US12168009B2 (en) | 2014-10-06 | 2024-12-17 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
-
1960
- 1960-10-10 GB GB3463260A patent/GB967177A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4473696A (en) * | 1982-10-07 | 1984-09-25 | Ici Americas Inc. | Synthesis of 2-substituted-5-methyl-pyridines |
| US4658031A (en) * | 1982-10-07 | 1987-04-14 | Ici Americas Inc. | Synthesis of 2-substituted-5-methyl-pyridines and intermediates therefor |
| US4687854A (en) * | 1982-10-07 | 1987-08-18 | Ici Americas Inc. | Bispiperidone precursor of 2-substituted-5-methyl-pyridines |
| US12168009B2 (en) | 2014-10-06 | 2024-12-17 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| TWI799435B (en) * | 2017-08-02 | 2023-04-21 | 美商維泰克斯製藥公司 | Processes for preparing compounds |
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