http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-669575-A
Outgoing Links
Predicate | Object |
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assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_4ddbd18acd6c9039c0eca2c3747b8c60 |
classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07B2200-07 |
classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C209-86 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C213-10 |
filingDate | 1949-04-04-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
publicationDate | 1952-04-02-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
publicationNumber | GB-669575-A |
titleOfInvention | Separation of stereoisomers of 1-(p-hydroxyphenyl)-2-(alpha-methyl-gamma-phenyl-propylamino)-propanol-(1) |
abstract | Stereoisomers of 1-(p-hydroxyphenyl)-2-(a -methyl - g - phenyl - propylamino) - propanol - 1 of melting points 111-112 DEG C. ("Base Ia") and 139-140 DEG C. ("Isobase Ib") are separated from mixtures thereof by fractional crystallization of the free bases (which may be liberated from their salts in situ) from aliphatic alcohols containing not more than 6 carbon atoms in the molecule, or by fractional crystallization of salts of the bases with fatty acids containing 2-4 carbon atoms in the molecule. The fractional crystallization of the free bases is preferably effected from methanol, in which case Base Ia separates first, after which Isobase Ib may be isolated from the mother liquor by prolonged standing in the cold (if necessary after further concentration) or by converting it to a salt, preferably the hydrochloride. When the initial mixture is in the form of salts of the bases (e.g. their hydrochlorides obtainable by hydrogenation of 1-(p-hydroxyphenyl)-2-aminopropanol-1 in the presence of benzylacetone, acidification with hydrochloric acid, evaporation and heating with acetone), separation may be effected by suspending the salts in methanol, adding an equimolecular quantity of methanolic alkali (e.g. sodium methylate, methanolic caustic soda or preferably methanolic caustic potash), filtering off the Base Ia which crystallizes out together with the alkali metal salt of the acid (which is then removed by washing with water), and recovering Isobase Ib as before. Alternatively, if the proportion of Isobase Ib hydrochloride exceeds about 60 per cent, the hydrochloride of Base Ia (with a minor proportion of its isomer) may be dis solved out by heating with a little aqueous methanol (or ethanol) or water, the resulting solution being treated as before and the residue of Isobase Ib hydrochloride being purified by further recrystallization or by way of the free base. The fractional crystallization of the fatty acid salts of the bases is preferably effected from diluted aqueous solutions of the fatty acids, though other solvents (e.g. methanol) may also be used. Examples illustrate the various embodiments of the invention. Specification 669,574 is referred to. |
priorityDate | 1948-04-09-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 30.