http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-595631-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_966a6c1f382ec9bcb5e3839dfd73e5b8 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-22 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-02 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-22 |
| filingDate | 1944-09-01-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1947-12-11-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-595631-A |
| titleOfInvention | Improvements in or relating to the preparation of piperidine derivatives |
| abstract | Compounds having the general formula <FORM:0595631/IV/1> wherein R1 represents hydrogen or a lower alkyl, hydroxy-alkyl, or an alkoxy-alkyl radical, X represents a radical of the structure <FORM:0595631/IV/2> wherein R2 represents a lower alkyl, a lower alkoxy or a hydroxy radical and R3 represents hydrogen, a lower alkyl or lower alkoxy or a hydroxy radical, or both R2 and R3 together form a methylenedioxy group and one of the radicals Y and Z represents hydrogen and the other a radical of the structure <FORM:0595631/IV/3> wherein R4 and R5 have meanings similar to those assigned to R2 and R3, are obtained preferably by condensing a 2.4- or 2.6-dimethylpyridine with a substituted benzaldehyde of the formula <FORM:0595631/IV/4> to yield a phenethenyl pyridine intermediate in which the two phenethenyl radicals carry identical substituents. The terms "lower alkyl" and "lower alkoxy" refer to radicals containing not more than eight carbon atoms. Products carrying phenyl ethyl radicals containing different substituents are obtained by condensing 1 mol. of 2.4- or 2.6-dimethylpyridine with 1 mol. of a substituted benzaldehyde, and subjecting the separated monophenethenyl derivative to a second condensation with a benzaldehyde containing other substituents. Specifically suitable benzaldehydes are anisaldehyde, p-ethoxybenzaldehyde, m- or p-tolualdehydes, vanillin, isovanillin, piperonal or m- or p-hydroxy benzaldehydes. The phenethenyl pyridine compounds are next subjected to two alternative treatments: (a) heating with an alkyl, hydroxyalkyl, alkoxyalkyl or aralkyloxyalkyl-arylsulphonate, e.g. methyl-, ethyl-, propyl-, hydroxyethyl-, ethoxyethyl-, or benzoxyethyl p-toluenesulphonate and reducing the resultant phenethenyl pyridinium aryl sulphonate with hydrogen in the presence of a catalyst such as platinum, palladium, nickel or copper chromite; (b) hydrogenating catalytically the di-phenethenyl pyridine compound to obtain the 1-unsubstituted piperidine derivative which may then be alkylated with an alkyl halide, an oxalkyl halide or an oxalkyl halide ether. The reaction products may be converted into salts by treating a solution of the base with the equivalent proportion of an acid, e.g. nitric, hydriodic, hydrobromic, acetic, lactic, or with normal or acid salts of dibasic or tribasic acids, e.g. tartaric, sulphuric, phosphoric, gluconic, citric. Numerous examples are given. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-2686784-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4569941-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-2626948-A |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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