GB653591A - Improvements in or relating to cyclic amino alcohols - Google Patents
Improvements in or relating to cyclic amino alcoholsInfo
- Publication number
- GB653591A GB653591A GB27575/48A GB2757548A GB653591A GB 653591 A GB653591 A GB 653591A GB 27575/48 A GB27575/48 A GB 27575/48A GB 2757548 A GB2757548 A GB 2757548A GB 653591 A GB653591 A GB 653591A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperidine
- methoxy
- solution
- methyl
- dihydroxy
- 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
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
A 1-(alkyl, aryl or aralkyl)-3-hydroxy-5-alkoxy piperidine is produced by reacting together at substantially 100 DEG C. a 1 : 2-epoxy-4-alkoxy-5- halo pentane and a primary alkyl, aryl or aralkylamine. The product may be dealkylated by treatment with hydrobromic acid to form a 1-(alkyl, aryl or aralkyl)-3 : 5-dihydroxy piperidine. When the amine employed is volatile the reaction may be effected in a sealed vessel. In examples: (1) 1 : 2-epoxy-4-methoxy-5-bromo-pentane is heated in a sealed tube at 100 DEG C. with anhydrous methyl amine. After extraction with the minimum of water, the solution is saturated with potash and the separated oil extracted with benzene. On distilling the dried solution, 1 - methyl - 3 - hydroxy-5-methoxy piperidine is obtained. The latter is converted to 1-methyl-3 : 5-dihydroxy piperidine by adding it to a solution of anhydrous hydrobromic acid in glacial acetic acid and heating to 100 DEG C. until there is no more evolution of methyl bromide. The temperature is then kept at 100 DEG to 110 DEG C. for one hour and the mixture dissolved in absolute alcohol and treated with hydrated barium hydroxide. The insoluble matter is filtered off and the solution distilled to yield the dihydroxy compound; (2) as in (1) but using ethylamine instead of methylamine, the product being 1-ethyl-3-hydroxy-5-methoxy-piperidine which is converted to 1-ethyl-3 : 5-dihydroxy piperidine by treatment with hydrobromic acid; (3) 1-phenyl-3-hydroxy-5-methoxy piperidine is obtained by heating the same starting material as in (1) with aniline. The halogen atom in the 1 : 2-epoxy-4-alkoxy-5-halopentane is preferably chlorine, bromine or iodine. 1 : 2 - Epoxy - 4 - methoxy - 5 - brom - pentane is obtained by the action of a solution of perbenzoic acid in chloroform at -5 DEG C. on 1-bromo-2-methoxy-4-pentene which is itself obtained by the action of N,N-dibromo-p-toluene sulphonamide on 1 : 4-pentadiene in methyl alcohol. The Specification as open to inspection under Sect. 91 is not restricted to reaction at a specified temperature and refers to the use of any dealkylating agent in the production of the 1-(alkyl, aryl, or aralkyl)-3,5 dihydroxy piperidine. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR653591X | 1947-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB653591A true GB653591A (en) | 1951-05-16 |
Family
ID=9005951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27575/48A Expired GB653591A (en) | 1947-11-07 | 1948-10-22 | Improvements in or relating to cyclic amino alcohols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB653591A (en) |
-
1948
- 1948-10-22 GB GB27575/48A patent/GB653591A/en not_active Expired
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