GB629196A - Piperidine derivatives - Google Patents
Piperidine derivativesInfo
- Publication number
- GB629196A GB629196A GB17997/47A GB1799747A GB629196A GB 629196 A GB629196 A GB 629196A GB 17997/47 A GB17997/47 A GB 17997/47A GB 1799747 A GB1799747 A GB 1799747A GB 629196 A GB629196 A GB 629196A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isopropyl
- piperidine
- cyclohexyl
- phenyl
- piperidone
- 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
Landscapes
- Hydrogenated Pyridines (AREA)
Abstract
Piperidine derivatives of the general formula <FORM:0629196/IV (b)/1> where R is a cyclohexyl or aryl group, R1 is a branched or non-branched alkyl group and R11 is hydrogen or a methyl group, are prepared by reacting the corresponding 1-alkyl-piperidone-(4) with an aryl-lithium compound in an inert solvent or diluent and acylating the addition product, said acylation being carried out after hydrolysis followed by hydrogenation in the case where a phenyl lithium compound is used and a cyclohexyl derivative is desired. The reaction with the aryl lithium compound takes place in inert solvents or diluents such as ether, benzene, cyclohexane, dioxane, isopropyl ether or pyridine. The acylation is conveniently carried out by reaction with an acyl halide or acid anhydride such as the chlorides or anhydrides of acetic or propionic acid in an inert solvent such as acetone or benzene; and acid binding agent such as pyridine or potassium carbonate may be present, or sulphuric acid and sodium acetate may be added. Hydrogenation to convert the phenyl group " R " into a cyclohexyl group is carried out by treatment with hydrogen, preferably under pressure in the presence of a hydrogenation catalyst, such as platinum, in a solvent such as water, methanol, ethanol, isopropanol, dioxane or ethyl acetate. The piperidine derivatives may be converted into their salts with organic or inorganic acids such as tartaric, maleic, citric, sulphuric, sulphonic or the hydrohalic acids. In examples: (1) 1-isopropyl-4-piperidone is added to phenyl lithium in benzol, the product is treated with propionic anhydride, and hydrochloric acid is added to give the hydrochloride of 1-isopropyl-4-phenyl-4-propionoxy-piperidine, which is converted to the free base by treatment with 1-isopropyl-4-piperidone and the resulting 1-isopropyl-4-phenyl-4-lithiumoxy-piperidine is decomposed with dilute hydrchloric acid to give 1-isopropyl-4-phenyl-4-hydroxy-piperidine which is converted to the hydrochloride, catalytically reduced to 1-isopropyl-4-cyclohexyl-4-hydroxypiperidine hydrochloride and finally treated with propionic anhydride to give 1-isopropyl-4-cyclohexyl - 4 - propionoxy - piperidine hydrochloride; and (3) by using 1 : 3-dimethyl-4-piperidone in place of 1-isopropyl-4-piperidone in the process of (2) there is obtained 1 : 3-dimethyl - 4 - cyclohexyl - 4 - propionoxy piperidine hydrochloride. Aryl-lithium compounds are prepared by reacting lithium metal with aromatic halogeno compounds such as bromobenzene and bromonaphthalene.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US629196XA | 1946-07-08 | 1946-07-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB629196A true GB629196A (en) | 1949-09-14 |
Family
ID=22045711
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB17997/47A Expired GB629196A (en) | 1946-07-08 | 1947-07-08 | Piperidine derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB629196A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3012030A (en) * | 1960-04-29 | 1961-12-05 | Paul A J Janssen | Lower alkyl esters of 1-cinnamyl-3-methyl-4-phenylpiperidine-4-carboxylic acid |
US3012037A (en) * | 1960-04-29 | 1961-12-05 | Paul A J Janssen | Esters of 3-methyl-4-phenyl-4-carboxypiperidine |
US3185702A (en) * | 1959-03-16 | 1965-05-25 | Lunsford Carl Dalton | Basic esters of 3-aryl-3-pyrrolidinols |
US3252994A (en) * | 1959-02-12 | 1966-05-24 | Mead Johnson & Co | 1, 2-dimethyl-3-benzyl-3-propionoxy-pyrrolidine |
US3256297A (en) * | 1958-04-02 | 1966-06-14 | Parke Davis & Co | 1, 2-dimethyl and 1, 2, 2 trimethyl-3-phenyl-3-propionyloxy pyrrolidines |
-
1947
- 1947-07-08 GB GB17997/47A patent/GB629196A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3256297A (en) * | 1958-04-02 | 1966-06-14 | Parke Davis & Co | 1, 2-dimethyl and 1, 2, 2 trimethyl-3-phenyl-3-propionyloxy pyrrolidines |
US3252994A (en) * | 1959-02-12 | 1966-05-24 | Mead Johnson & Co | 1, 2-dimethyl-3-benzyl-3-propionoxy-pyrrolidine |
US3185702A (en) * | 1959-03-16 | 1965-05-25 | Lunsford Carl Dalton | Basic esters of 3-aryl-3-pyrrolidinols |
US3012030A (en) * | 1960-04-29 | 1961-12-05 | Paul A J Janssen | Lower alkyl esters of 1-cinnamyl-3-methyl-4-phenylpiperidine-4-carboxylic acid |
US3012037A (en) * | 1960-04-29 | 1961-12-05 | Paul A J Janssen | Esters of 3-methyl-4-phenyl-4-carboxypiperidine |
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