GB1196958A - 2,2,6,6-Tetrasubstituted-4-Substituted Methylene Piperidinenitroxides and process for preparing the same - Google Patents
2,2,6,6-Tetrasubstituted-4-Substituted Methylene Piperidinenitroxides and process for preparing the sameInfo
- Publication number
- GB1196958A GB1196958A GB3185867A GB3185867A GB1196958A GB 1196958 A GB1196958 A GB 1196958A GB 3185867 A GB3185867 A GB 3185867A GB 3185867 A GB3185867 A GB 3185867A GB 1196958 A GB1196958 A GB 1196958A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperidone
- cyano
- prepared
- tetramethyl
- alkali metal
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,196,958. 2,2,6,6-tetra-alkyl piperidine nitroxides. SANKYO CO. Ltd. 11 July, 1967 [16 Aug., 1966; 5 Oct., 1966], No. 31858/67. Heading C2C. Novel compounds of the general formula wherein R 1 and R 2 are alkyl groups and R 3 and R 4 are each cyano, carboxyl, alkoxycarbonyl, carbamoyl, aliphatic or aromatic acyl groups or aryl groups are prepared by reacting a compound of the general formula with a compound R 3 -CH 2 -R 4 in the presence of a basic condensing agent. The compounds, except where R 3 and R 4 are cyano groups may also be prepared by reacting a 2,2-dimethyl 6,6-dialkyl-4-piperidone with a compound R 3 -CH 2 -R 4 and then treating the product with a peroxide. The basic catalyst may be a hydroxide or carbonate of an alkali metal, an alkaline earth hydroxide, alkali metal alcoholate alkali metal amide or hydride. The perioxide employed is preferably H 2 O 2 but may be an organic peracid, e.g. peracetic or perbenzoic acid. In the Examples 2,2,6,6-tetramethyl-4- oxopiperidine nitroxide is reacted with (1) benzyl cyanide (2) malononitrile, (3) ethyl cyanoacetate to give 4-(α-cyano-benzylidine)-, 4-(α,α-dicyanomethylene)-, and 4-(α-cyano-α- ethoxycarbonylmethylene)- 2,2,6,6.tetramethyl piperidine nitroxide respectively using the first procedure. The second method was employed to prepare 4-(α-carbamoylbenzlidene) -, 4- (α- carbamoyl - α - ethoxycarbonylmethylene)- and 4-(α,α-dicarbamoyl-methylene)- 2,2,6,6-tetramethyl piperidine nitroxide from 2,2,6,6- tetramethyl-4-piperidone. The starting material for the first method may be prepared from diacetone alcohol and a ketone of the formula R 1 R 2 C = O in the presence of NH 3 and a Lewis acid followed by treatment of the tetraalkyl-4-piperidone with H 2 O 2 or an organic peracid. The starting material for the second method, tetraalkyl-4- piperidone is prepared as described above.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5343566 | 1966-08-16 | ||
| JP6552266 | 1966-10-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1196958A true GB1196958A (en) | 1970-07-01 |
Family
ID=26394144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3185867A Expired GB1196958A (en) | 1966-08-16 | 1967-07-11 | 2,2,6,6-Tetrasubstituted-4-Substituted Methylene Piperidinenitroxides and process for preparing the same |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1695749A1 (en) |
| GB (1) | GB1196958A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113258109A (en) * | 2021-05-21 | 2021-08-13 | 吉林大学 | Hybrid proton exchange membrane based on polyacid/piperidine aryl copolymer and preparation method thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1606259B1 (en) * | 2003-03-27 | 2014-06-25 | Basf Se | Process for the oxidation of secondary amines into the corresponding nitroxides |
| EP3255039B1 (en) | 2016-06-10 | 2018-12-12 | Evonik Degussa GmbH | Method for the preparation of 2- (2,2,6,6-tetramethylpiperidine-4-yl) propane-1,3-diamine |
-
1967
- 1967-07-11 GB GB3185867A patent/GB1196958A/en not_active Expired
- 1967-07-15 DE DE19671695749 patent/DE1695749A1/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113258109A (en) * | 2021-05-21 | 2021-08-13 | 吉林大学 | Hybrid proton exchange membrane based on polyacid/piperidine aryl copolymer and preparation method thereof |
| CN113258109B (en) * | 2021-05-21 | 2022-07-15 | 吉林大学 | Hybrid proton exchange membrane based on polyacid/piperidine aryl copolymer and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1695749A1 (en) | 1971-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |