GB773183A - Piperidine derivatives and a process for the preparation thereof - Google Patents
Piperidine derivatives and a process for the preparation thereofInfo
- Publication number
- GB773183A GB773183A GB33748/55A GB3374855A GB773183A GB 773183 A GB773183 A GB 773183A GB 33748/55 A GB33748/55 A GB 33748/55A GB 3374855 A GB3374855 A GB 3374855A GB 773183 A GB773183 A GB 773183A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thenyl
- methyl
- bromoaniline
- bromo
- aniline
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0773183/IV(b)/1> (wherein R1 represents H, Cl or Br, R2 represents H or Br, R3 represents CH3 and Y represents -CH2- or -C2H4-), and the preparation thereof and of compounds in which Y represents a direct linkage by condensing a compound of the general formula <FORM:0773183/IV(b)/2> with a compound of the general formula <FORM:0773183/IV(b)/3> (wherein Halogen represents chlorine or bromine), preferably at elevated temperature in an inert solvent (e.g. toluene, xylene or chlorobenzene) and in the presence of an alkali metal hydroxide or amide as condensation agent. The products are useful as antihistaminics and/or sedatives. In examples: (1) N-(2-thenyl)-m-bromoaniline is heated with 2-(N-methyl-piperidyl - 21) - 1 - chloroethane in xylol in the presence of sodamide to produce N-(2-thenyl)-N - [2 - (N1 - methylpiperidyl - 21) - ethyl - 1] - m-bromoaniline, which converted to its dihydrochloride; (2) N-(5-bromo-2-thenyl)-aniline similarly yields N - (5 - bromo - 2 - thenyl) - N - [2 - (N1 - methylpiperidyl - 21) - ethyl - 1] - aniline (but using sodium hydroxide instead of sodamide); (3) N - (5 - bromo - 2 - thenyl) - m - bromoaniline is reacted as in (2) to give N-(5-bromo - 2 - thenyl) - N - [2 - (N1 - methylpiperidyl - 21) - ethyl - 1] - m - bromoaniline, which is converted to its dihydrochloride; (4) N - (2 - thenyl) - aniline is reacted with N-methyl-4-bromopiperidine as in (1) to produce N - methyl - 4 - amino - N1 - phenyl - N1 - (2 - thenyl)-piperidine, which is converted to its tartrate; (5) N-methyl-3-chloromethylpiperidine similarly yields N-(2-thenyl)-N-(N1-methyl-b -pipecolyl)-aniline, which is converted to its hydrochloride; (6) 2-(N-methylpiperidyl-21)-1-chloroethane similarly gives N-(2-thenyl-N-[2-(N1 - methylpiperidyl - 21) - ethyl - 1] - aniline and its hydrochloride; similarly prepared are: (7) and (8) N-methyl-4-amino-N1-phenyl-N1-(5-chloro- and 5-bromo-2-thenyl)-piperidine and their tartrates; (9) and (10) N-methyl-4-amino-N1 - (m - bromophenyl) - N1 - (5 - bromo - 2 - thenyl)- and -N1-(2-thenyl)-piperidine. Starting materials. N-(2-Thenyl)-m-bromoaniline is prepared by warming m-bromoaniline with 2-thenyl chloride in aqueous sodium bicarbonate solution. N-(5-Bromo-2-thenyl)-aniline and -m-bromoaniline (the hydrochlorides of which are described) are prepared by similarly condensing 5-bromo-2-thenyl chloride with aniline and m - bromoaniline respectively. N - Methyl - 4 - bromopiperidine (the hydrobromide of which is described) is prepared by treating N - methyl - 4 - hydroxypiperidine with thionyl bromide. Specification 717,227 is referred to.ALSO:As antihistamines and/or sedatives may be employed piperidine derivatives of the general formula <FORM:0773183/VI/1> (wherein R1 represents H, Cl or Br, R2 represents H or Br, R3 represents CH3 and Y represents - CH2 -, - C2H4 - or a direct linkage) or their salts. Thus N - methyl-4 - amino - N1 - phenyl - N1 - (2 - thenyl) - piperidine may be used for combatting allergic diseases by administering it orally, intravenously in combination with a soluble calcium salt, or externally in the form of an ointment. Compounds in which Y is - CH2 - or - C2H4 - may be administered orally or parenterally, e.g. intermuscularly, when simultaneous antihistaminic and sedative action is desired. Specification 717,227 [Group IV(b)] is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH773183X | 1954-11-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB773183A true GB773183A (en) | 1957-04-24 |
Family
ID=4535581
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB33748/55A Expired GB773183A (en) | 1954-11-25 | 1955-11-24 | Piperidine derivatives and a process for the preparation thereof |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE543032A (en) |
CH (1) | CH344060A (en) |
DK (1) | DK91018C (en) |
FR (1) | FR1161379A (en) |
GB (1) | GB773183A (en) |
-
0
- BE BE543032D patent/BE543032A/xx unknown
-
1955
- 1955-10-19 CH CH344060D patent/CH344060A/en unknown
- 1955-11-22 DK DK381755A patent/DK91018C/en active
- 1955-11-24 FR FR1161379D patent/FR1161379A/en not_active Expired
- 1955-11-24 GB GB33748/55A patent/GB773183A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DK91018C (en) | 1961-06-05 |
BE543032A (en) | |
FR1161379A (en) | 1958-08-28 |
CH344060A (en) | 1960-01-31 |
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