http://rdf.ncbi.nlm.nih.gov/pubchem/patent/IE-32936-B1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_966a6c1f382ec9bcb5e3839dfd73e5b8 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-70 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D213-30 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-82 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D221-26 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D213-30 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D221-26 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-70 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-82 |
| filingDate | 1968-12-30-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1974-01-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | IE-32936-B1 |
| titleOfInvention | Benzomorphan derivatives |
| abstract | 1,198,750. Benzomorphan derivatives. F. HOFFMANN-LA ROCHE & CO. A.G. 20 Dec., 1968 [5 Jan., 1968], No. 60561/68. Heading C2C. Benzomorphan derivatives of the Formula (II) are prepared by cyclizing a tetrahydropyridine compound of the formula wherein R is H, C 1-8 alkyl or acyl; R<SP>1</SP> is a -COR<SP>2</SP> or -SO 2 R<SP>3</SP> group; R<SP>2</SP> is H, C 1-8 alkyl or aryl; and R<SP>3</SP> is C 1-8 alkyl or aryl, or a corresponding 4 - hydroxy - hexahydropyridine derivative by treatment with an acid catalyst and, if desired, the product is further treated so as to remove or modify the substituent R<SP>1</SP> and/or to convert the -OR group into a hydroxy group. Benzomorphans of Formula (II) in which R<SP>1</SP> is -CHO or -SOR<SP>3</SP> and R, R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are as above-defined are novel. The compounds of Formula (II) can be treated with alkali hydroxide or an acid in methanol to replace R<SP>1</SP> by H, then N-methylated with HCHO and hydrogen over Raney nickel. N-alkylated benzomorphans can also be obtained by reducing the R<SP>1</SP> group with LiAlH 4 . Optical antipodes can be obtained by resolution by known methods, e.g. by formation of tartrate or brucine salt. Intermediates are obtained as follows: p- Methoxybenzyl chloride is reacted with 3,4- lutidine in acetonitrile to yield 1-(4-methoxybenzyl) - 3,4 - dimethyl - pyridinium chloride which was then reacted with a Grignard reagent obtained from p-methoxybenzyl chloride to form 1,2 - di - (4 - methoxybenzyl) - 3,4- dimethyl - 1,2 - dihydro - pyridine and the latter is reduced with NaBH 4 and converted to 1,2- di - (4 - methoxybenzyl) - 3,4 - dimethyl - 1,2,5,6- tetrahydropyridine HCl which is hydrogenated to 2 - (4 - methoxybenzyl) - 3,4 - dimethyl -1,2,5,6- tetrahydropyridine HCl and reaction with methyl formate yields 3,4-dimethyl-2-(4-methoxy - benzyl) - 5,6 - dihydro - 1(2H) - pyridinecarboxaldehyde.n[GB1198750A] |
| priorityDate | 1968-01-05-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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Total number of triples: 49.