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filingDate 1976-05-05-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1978-03-08-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1502933-A
titleOfInvention Aniline derivatives
abstract 1502933 Aniline derivatives and intermediates thereof UPJOHN CO 5 May 1976 [12 May 1975] 18333/76 Addition to 1479333 Heading C2C The invention comprises certain compounds containing the grouping A-O-Ar-N< and acid addition salts thereof, wherein A is an adamantyl or diamantyl group and Ar is an optionally substituted p-phenylene radical. N - methyl - 4<SP>1</SP> - (1 - adamantyloxy)acetanilide, 41 - (1 - adamantyloxy) - 2<SP>1</SP> - fluoroacetanilide, 4<SP>1</SP> - (1 - diamantyloxy)acetanilide and 4<SP>1</SP> - (1- adamantyloxy) - 3<SP>1</SP> - fluoroacetanilide are obtained by reacting the corresponding amines with acetic anhydride. 1-[4-Adamantyloxy-2- fluorophenyl]pyrrolidine, 1 - [4 - (1 - adamantyloxy) - 2,6 - dimethylphenyl]pyrrolidine, 1 - [4 - (1- diamantyloxy)phenyl]pyrrolidine and N - [4 - (1- adamantyloxy) - 3 - fluorophenyl]pyrrolidine are obtained by reacting the corresponding amines with dibromobutane. 4 - (Adamantyloxy) - 2- methyl - 6 - [(methylthio)methyl]aniline is obtained by reacting the corresponding 6- unsubstituted compound with dimethyl sulphide. 4 - (1 - Adamantyloxy) - 2,6 - dimethylaniline is obtained by desulphurization of the corresponding 6 - methylthiomethyl compound. 4 - (1 - Diamantyloxy)aniline is obtained by brominating diamantane, hydrolysing the 1-bromodiamantane, reacting the 1- diamantanol so produced with p-fluoro-nitrobenzene and reducing the 4-(1-diamantyloxy) nitrobenzene so produced. 4 - (1 - Adamantyloxy) - 3 - fluoroaniline is obtained by nitrating 1,2 - difluorobenzene, reacting the 3,4-difluoronitrobenzene with 1-adamantanol and reducing the 4 - (1 - adamantyloxy) - 3 - fluoronitrobenzene so produced. N - [4 - (1 - adamantyloxy)phenyl]pyrrolidine hydrochloride is obtained by reacting the free base with hydrogen chloride. A pharmaceutical composition comprises one of the above compounds or a salt thereof together with a pharmaceutically acceptable carrier.
priorityDate 1975-05-12-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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