http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-825564-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_c902faf6ae746c51fc8010672fc22894 |
| filingDate | 1956-07-13-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1959-12-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-825564-A |
| titleOfInvention | 2-spiro-substituted pyrrolidines |
| abstract | The invention comprises compounds of the general formula <FORM:0825564/IV (b)/1> wherein m is one or two, R1 and R11 are hydro-gen or methyl and R111 is hydroxyalkyl of the formula CnH2nOH or haloalkyl of the formula CvH2nX, wherein n is two to six, X is chlorine, bromine or iodine, and the alkylene group CnH2n may be straight or branched and has at least two carbon atoms between the valencies, and the preparation thereof by heating a spiropyrrolidine having the general formula <FORM:0825564/IV (b)/2> with a halohydrin, alkylene oxide or a halo ester followed by reduction of the thus-produced pyrrolidyl alkanoic acid ester with lithium aluminium hydride to produce compounds wherein R111, in the general formula of the products, is hydroxyalkyl, and then, if desired, reacting the latter compound with thionyl bromide or chloride, phosphorus tribromide or trichloride or hydrogen iodide to produce a compound wherein R111 is a haloalkyl. In examples, spiro-[cyclohexane-1,21-pyrrolidine] is reacted with ethylenechlorohydrin to form betaspiro - [cyclohexane - 1,21 - pyrrolidyl - 11] - ethanol or with trimethylene chlorohydrin to give gamma - spiro - [cyclohexane - 1,21 - pyrro-lidyl-11]-propanol, which in turn are treated with thionyl chloride to give beta-spiro - [cyclo-hexane - 1,21 - pyrrolidyl - 11] - ethyl chloride and gamma - spiro - [cyclohexane - 1,21 - pyrro-lidyl - 11] - propyl chloride. The hydrochlorides of the ethanol and both halides are also prepared. In further examples, 2-[spiro-(cyclo-hexane - 1,21 - pyrrolidyl)] - propanol is prepared by reacting ethyl alpha-bromopropionate with spiro - (cyclohexane - 1,21 - pyrrolidine) to form ethyl alpha-[spiro-(cyclohexane-1,21-pyrro-lidyl)]-propionate and reducing this with lithium aluminium hydride, and beta - spiro - (cyclo-hexane - 1,21 - pyrrolidyl - 11) - ethanol is prepared by bubbling ethylene oxide through spiro-(cyclohexane-1,21-pyrrolidine) in benzene. The alkanols of the invention may be esterified with an aryl acid chloride or bromide in benzene to produce compounds of the general formula <FORM:0825564/IV (b)/3> wherein Aryl is an aryl radical, e.g. phenyl, biphenylyl, tolyl, xylyl, p-aminophenyl, p-propoxyphenyl, o,o1 - dimethyl - p - propoxyphenyl, or they may be esterified with a disubstituted acetic acid chloride or bromide in benzene to produce compounds of the formula <FORM:0825564/IV (b)/4> wherein A and B are alike or different and are alkyl (one to eight carbon atoms), cycloalkyl, cycloalkenyl, or aryl as defined above. Specifications 825,561 and 825,563 also are referred to. |
| priorityDate | 1955-07-18-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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