GB673633A - Improvements in or relating to the production of substituted diamines and ª‡-pyridyl-ª‡-thenylamine intermediates therefor - Google Patents
Improvements in or relating to the production of substituted diamines and ª‡-pyridyl-ª‡-thenylamine intermediates thereforInfo
- Publication number
- GB673633A GB673633A GB27882/47A GB2788247A GB673633A GB 673633 A GB673633 A GB 673633A GB 27882/47 A GB27882/47 A GB 27882/47A GB 2788247 A GB2788247 A GB 2788247A GB 673633 A GB673633 A GB 673633A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyridyl
- appropriate
- thenylamine
- methyl
- general formula
- 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)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Diamines of the general formula <FORM:0673633/IV (b)/1> (wherein R1 and R2 each represent hydrogen or an alkyl group of 1-4 carbon atoms, or R2 may also represent chlorine, bromine or iodine, A represents an alkylene group of 2-11 carbon atoms, and R3 and R4 represent alkyl or aralkyl groups or may be joined to form a ring, and together contain a total of not more than 11 carbon atoms) are manufactured by treating at reaction temperatures, in the presence of a solvent which is or contains an acid-binding agent, an a -pyridyl-a 1-thenylamine with an o -R3,R4-aminoalkyl halide. Preferably the halide is a chloride and the reaction is carried out in an inert hydrocarbon solvent (e.g. benzene, toluene, xylene or petroleum ether) in the presence of an alkali metal (e.g. sodium) amide or hydride. The products are useful as chemical intermediates, and in some cases themselves possess physiological activity, e.g. some have antihistaminic and antispasmodic and some local anaesthetic properties. They may be converted into salts (e.g. hydrohalides, sulphates, phosphates, oxalates, succinates, fumarates, maleates, tartrates, gluconates, citrates or picrates) and quaternary ammonium compounds. Examples and a list illustrate the following meanings of the various symbols: R1=hydrogen and g -methyl, R2=hydrogen, b 1-methyl and a 11-bromo, A = -(CH2)2-, -(CH2)3-, -(CH2)11- and -CH2-C(CH3)2-CH2-, R3=methyl, ethyl or n-butyl, R4= as R3, or benzyl, or R3+R4+N = piperidino or morpholino. Specification 606,181 is referred to. a - Pyridyl - a 1 - thenylamines of the general formula <FORM:0673633/IV (b)/2> are manufactured by reacting an appropriate a -aminopyridine with an appropriate a -halomethylthiophene, or with an appropriate thiophene-a -aldehyde in the presence of a reducing agent (especially formic acid), or by reacting an appropriate a -halopyridine with an appropriate a -thenylamine. Examples describe the preparation of a -pyridyl-a 1-thenylamine and N - (a - pyridyl) - N - (a 11 - bromo - a 1 - thenyl) amine. Thiophene-a -aldehydes of the general formula <FORM:0673633/IV (b)/3> are obtainable by reacting a thiophene compound (e.g. a -bromothiophene) with an N-substituted formanilide (e.g. N-methyl-, N-ethyl- or N-phenyl-formanilide) in the presence of phosphorus oxychloride. The Specification as open to inspection under Sect. 91, comprises also the manufacture of compounds of the general formula above in which A may be a hydrocarbon radical other than alkylene, and R3 and R4 may be hydrogen, and the use of the processes of Specification 672,872 and of the additional processes described in that Specification (as open to inspection under Sect. 91). Additional examples are given. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US274614XA | 1946-10-17 | 1946-10-17 | |
US250947XA | 1947-09-25 | 1947-09-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB673633A true GB673633A (en) | 1952-06-11 |
Family
ID=26699260
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB27882/47A Expired GB673633A (en) | 1946-10-17 | 1947-10-07 | Improvements in or relating to the production of substituted diamines and ª‡-pyridyl-ª‡-thenylamine intermediates therefor |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE476794A (en) |
CH (1) | CH274614A (en) |
DE (1) | DE970796C (en) |
GB (1) | GB673633A (en) |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE471555A (en) * | 1943-06-22 | |||
FR53854E (en) * | 1943-06-22 | 1947-01-10 |
-
0
- BE BE476794D patent/BE476794A/xx unknown
-
1947
- 1947-10-07 GB GB27882/47A patent/GB673633A/en not_active Expired
- 1947-10-17 CH CH274614D patent/CH274614A/en unknown
-
1949
- 1949-01-01 DE DEP30172D patent/DE970796C/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
CH274614A (en) | 1951-04-15 |
DE970796C (en) | 1958-10-30 |
BE476794A (en) |
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