http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1299670-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_5fb3689bb224dbbee5f993de522c694e |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-78 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-86 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-52 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-48 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-46 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-74 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-74 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-48 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-46 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-52 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-86 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-78 |
| filingDate | 1970-06-01-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_dc8bfaad2cab728d57cbd89740599ddb http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_ce9b7c2c16216bf7ebf9d9ee9ee8b0da |
| publicationDate | 1972-12-13-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1299670-A |
| titleOfInvention | 2-benzyl-4-piperidine compounds |
| abstract | 1299670 2-Benzyl-4-piperidin-ones and -ols ACF CHEMIEFARMA NV 1 June 1970 [4 June 1969(2)] 22736/72 Divided out of 1299669 Heading C2C The invention comprises compounds of Formula (I) in which X is OH and Y is R 2 , or X and Y together denote a single O atom linked to the ring by a double bond, and each R, which may be the same or different, is CH 3 or C 2 H 5 or together in combination with the ring carbon atom to which they are attached represent a cycloaliphatic ring, R 1 is H, alkyl or aryl, R 2 is alkyl, alkinyl, aryl, aralkyl, or heteroaryl group, and R 3 is H, OH or alkoxy, or salts thereof. The piperidinols may be obtained by reducing the corresponding 4-piperidones in which X and Y together O or by reacting the 4- piperidone with an alkyl, alkinyl, aryl, aralkyl or heteroaryl metal compound. The piperidones may be obtained by reacting a #-keto estic of Formula (III) where R 3 <SP>1</SP> is H or alkoxy, with benzylamine, catalytically hydrogenating the resulting Schiff base to form a benzylamino ester of Formula (V) catalytically hydrogenolysing the latter to give a #-amino ester of Formula (VI) reacting the product with an alkyl acrylate or alkyl #-halopropionate, followed, if desired, by substitution on the nitrogen atom to give a 3,3<SP>1</SP>-iminodipropionic acid ester (VII) effecting a Duckmann cyclization reaction on the latter to form an alkyl 4-OXO-3-piperidine carboxylate of Formula (VIII) and hydrolysing and decarboxylating the latter to form the 2-benzyl-4-piperidone. Alternatively, this product may be obtained by the steps of acylating a propionic estic having a secondary amino group at the # position with an acid chloride of a mono ester of a dialkyl malonic acid or a 1,1-cylcoalkanedicarboxylic acid to form an amido dicarboxylic ester (IX) wherein the R 4 groups are equal or different alkyl groups and R 1 <SP>1</SP> is an alkyl or aralkyl group, effecting a Dieckmann cyclization to form a 1 - R 1 <SP>1</SP> -5,5 - R - 4,6 - dioxo - 3- piperidinecarboxylate, hydrolysing and decarboxylating the latter to form a 1-R 1 <SP>1</SP>-5,3-R- 2,4-piperidinedione, protecting the 4-carbonyl group by converting it to a 4-ketal, reacting the product with an optionally substituted benzyl lithium to form a 2-benzylidene piperidine and reducing the latter and regenerating the 4-oxo group to form a 2-benzyl-4-piporidone (XIV) and optionally converting R 1 <SP>1</SP> in to R 1 and/or R 3 <SP>1</SP> in to R 3 . |
| priorityDate | 1969-06-04-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 46.