GB720198A - Manufacture of new dioxopiperidines - Google Patents
Manufacture of new dioxopiperidinesInfo
- Publication number
- GB720198A GB720198A GB3744/52A GB374452A GB720198A GB 720198 A GB720198 A GB 720198A GB 3744/52 A GB3744/52 A GB 3744/52A GB 374452 A GB374452 A GB 374452A GB 720198 A GB720198 A GB 720198A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- dioxopiperidine
- mononitrile
- diacid
- ethyl
- 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
- 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
- C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
- C07D211/84—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 two 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 directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises 2 : 6-dioxopiperidines of the general formula <FORM:0720198/IV (b)/1> (wherein R1 represents an aliphatic hydrocarbon residue of 1-3 carbon atoms, R2 represents a phenyl residue which is unsubstituted or substituted by a halogen atom, and R3 represents hydrogen or an aliphatic hydrocarbon residue of 1-3 carbon atoms), which may be prepared from 2-R1, R2-disubstituted pentane-1:5-diacids or their functional derivatives (e.g. by reacting the acids or their functional derivatives, e.g. halides, with ammonia or amines, or by intramolecular acylation, by the action of condensing agents, of the monoamides of the acids or their functional derivatives, which may be formed in situ, e.g. from the mono- or di-nitriles or nitrile esters, or by heating the diamides, diammonium salts or mononitrile ammonium salts of the acids). When the product is unsubstituted in the 1-position, an aliphatic hydrocarbon residue may be subsequently introduced there, e.g. by the action of reactive esters of alcohols or of aliphatic diazo compounds (preferably in the presence of condensing agents capable of converting the dioxopiperidines into metal derivatives, e.g. alkali or alkaline-earth metals or their amides, hydrides, hydrocarbons or alcoholates). The products are useful as anticonvulsive agents. In examples: (1) 2-phenyl-2-ethylpentane-1 : 5-diacid 1-mononitrile is heated with glacial acetic acid and concentrated sulphuric acid to produce 3 - phenyl - 3 - ethyl - 2 : 6 - dioxopiperidine; (2) 2-phenyl-2-isopropylpentane-1 : 5-diacid 1-mononitrile similarly yields 3-phenyl-3-isopropyl-2 : 6-dioxopiperidine; (3) the 1-mononitrile in (1) is replaced by the 1-monoamide; (4) the product of (1) is warmed with sodamide in toluene and the product heated with methyl iodide under pressure, producing 1 - methyl - 3 - phenyl - 3 - ethyl-2 : 6-dioxopiperidine; (5) n-propyl bromide similarly gives 1 - n - propyl - 3 - phenyl - 3-ethyl - 2 : 6 - dioxopiperidine; (6) 2 - p - chlorophenyl - 2 - ethylpentane - 1 : 5 - diacid 5-monomethyl ester 1-mononitrile is heated with glacial acetic acid and 85 per cent sulphuric acid to form 3-p-chlorophenyl-3-ethyl-2 : 6-dioxopiperidine; (7) 2-phenyl-2-methylpentane-1 : 5-diacid 5-monomethyl ester 1-mononitrile similarly yields 3-phenyl-3-methyl-2 : 6-dioxopiperidine; (8) the product of (6) is methylated as in (4) except that dioxan is used instead of toluene as solvent. The aliphatic hydrocarbon residue may also be an unsaturated radical, e.g. allyl. 2 - Phenyl - 2 - ethyl - and - 2 - isopropylpentane - 1 : 5 - diacid 1 - mononitriles are obtainable by condensing a -phenylbutyronitrile or a -phenyl-b -methylbutyronitrile with methyl acrylate and hydrolysing the resulting monomethyl ester mononitriles. 2 - p - Chlorophenyl - 2 - ethyl - and 2 - phenyl-2 - methyl - pentane - 1 : 5 - diacid 5 - monomethyl ester 1-mononitriles are obtainable similarly (but omitting the hydrolysis) from a -(p - chlorophenyl) - butyronitrile and a -phenylpropionitrile respectively.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH720198X | 1951-02-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB720198A true GB720198A (en) | 1954-12-15 |
Family
ID=4531477
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3744/52A Expired GB720198A (en) | 1951-02-13 | 1952-02-12 | Manufacture of new dioxopiperidines |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB720198A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4839370A (en) * | 1986-07-31 | 1989-06-13 | Asta-Pharma Ag | Novel derivatives of 3-aryl-3-cycloalkyl-piperidine-2,6-dione |
-
1952
- 1952-02-12 GB GB3744/52A patent/GB720198A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4839370A (en) * | 1986-07-31 | 1989-06-13 | Asta-Pharma Ag | Novel derivatives of 3-aryl-3-cycloalkyl-piperidine-2,6-dione |
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