GB1468349A - 10-bornanamine and 7,7-dimethyl-norbornan-1-amine and derivatives thereof - Google Patents
10-bornanamine and 7,7-dimethyl-norbornan-1-amine and derivatives thereofInfo
- Publication number
- GB1468349A GB1468349A GB1089473A GB1089473A GB1468349A GB 1468349 A GB1468349 A GB 1468349A GB 1089473 A GB1089473 A GB 1089473A GB 1089473 A GB1089473 A GB 1089473A GB 1468349 A GB1468349 A GB 1468349A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- substituted
- amine
- compound
- reacting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
Abstract
1468349 10-Bornanamine and 7,7-dimethylnorbornan - 1 - amine and derivatives thereof GLAXO LABORATORIES Ltd 6 March 1974 [6 March 1973] 10894/73 Heading C2C [Also in Division A5] Novel 7,7 - dimethyl - [2,2,1] - bicycloheptanes having at the 1-position a group R and the physiologically acceptable salts thereof, wherein R is an amino- or aminomethyl group having a basic nitrogen atom and is substituted at the amino nitrogen atom (via a single or double bond) and/or at the 10-carbon atom by one or more aliphatic, cycloaliphatic, araliphatic, phenyl or substituted phenyl groups or, in the case of the amino group, by a heterocyclic group in which the nitrogen atom of the amino group forms part of the heterocyclic ring, or, in the case of N-substituted aminomethyl, by an oxo group at the 10-carbon atom, may be prepared (a) when the group R has a methylene group in an α-position in relation to the 1 or 10-nitrogen atom, by reducing the corresponding amide, (b) when R is a methylamino group, by reducing an ester of the coresponding carboxyamino compound, (c) when R is as in (b), reductively methylating the corresponding primary amine, (d) when R is an aliphatic or araliphatic imino or iminomethyl in which the methyl is optionally substituted by condensing the corresponding primary amine with an aldehyde or ketone, (e) when said compound is 1,3,5-tris-(bornan-10- yl)-1,3,5-hexahydrotriazine by reacting 10- bornanamine with formaldehyde, (f) when R is an aminomethyl group in which one of the hydrogen atoms on the methyl carbon atom is substituted by reducing the corresponding ketoxime, (g) when the 1 or 10-nitrogen atoms of R bears a phenyl or substituted phenyl substituent, by reacting the corresponding amine with a benzyne, (h) when the 1- or 10-nitrogen atoms of R is mono- or di-substituted by an aliphatic, cycloaliphatic or araliphatic group, by reacting the corresponding primary or secondary amine with a compound R<SP>5</SP>X where R<SP>5</SP> is an aliphatic, cycloaliphatic or araliphatic group and X is a readily eliminatable group, (i) when the 1- or 10-nitrogen of R forms part of a hydroxy-substituted heterocyclic ring which contains at least 3 carbon atoms, by cyclising a compound of the invention in which the nitrogen atom of R is substituted by a hydroxyalkyl group carrying a readily eliminatable group, there being at least 3 carbon atoms between the nitrogen and the amino group and the readily eliminatable group, (j) when R is aminomethyl in which the methyl group is substituted, by reducing the corresponding substituted nitromethyl compound, (k) when the 1-or 10-nitrogen atom of R is substituted by an aminoacyl group (the amino group of which is unsubstituted or substituted by one or two alkyl groups), by reacting the corresponding haloacyl compound with ammonia or mono- or dialkyl-amine, (d) when the 1- or 10-nitrogen atom of R forms part of a heterocyclic ring, by reacting the corresponding unsubstituted amine with a compound XR<SP>7</SP>X where X is a readily eliminatable group and R<SP>7</SP> is a divalent alkylene group (which may be interrupted by O or S) or a cyclic group bearing two mono-valent alkylene groups; or (m) when the 1- or 10-nitrogen of R is substituted by an aliphatic or araliphatic group, by reducing the compound in which the said nitrogen atom is linked to said group by a double bond. The various amide intermediates used as starting materials in process (a) are prepared by reaction of the corresponding acid chloride and amine. Similarly 10-bromoacetamido-bornane and 1 - bromoacetamido - 7,7 - dimethyl norbornane are prepared by reacting 10-Bornanamine or 1- amino - 7,7 - dimethyl - norbornane with bromoacetylbromide. 7,7 - Dimethylnorbornyl - 1 - methyl ketone oxime is prepared by reacting 7,7-dimethyl norbornane-1-carboxylic acid with methyl lithium to form 7,7-dimethylnorbornyl-1-methyl ketone followed by reaction with hydroxylamine hydrochloride.
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1089473A GB1468349A (en) | 1973-03-06 | 1973-03-06 | 10-bornanamine and 7,7-dimethyl-norbornan-1-amine and derivatives thereof |
CA194,054A CA1064928A (en) | 1973-03-06 | 1974-03-05 | 10-bornanamine, and 7,7-dimethylnorbornan-1-amines derivatives |
CH309874A CH616646A5 (en) | 1973-03-06 | 1974-03-05 | Process for the preparation of novel bornane derivatives |
JP2560374A JPS5029547A (en) | 1973-03-06 | 1974-03-05 | |
BE141644A BE811876A (en) | 1973-03-06 | 1974-03-05 | NEW BORNANE DERIVATIVES AND THEIR PREPARATION |
FR7407444A FR2220260B1 (en) | 1973-03-06 | 1974-03-05 | |
IE46174A IE39712B1 (en) | 1973-03-06 | 1974-03-05 | 10-bornanamine and 7,7-dimethylnorbornan-1-amine and derivatives |
DE19742410492 DE2410492A1 (en) | 1973-03-06 | 1974-03-05 | NEW BORNAND DERIVATIVES, THE PROCESS FOR THEIR PRODUCTION AND THEIR USE |
AT179774A AT353247B (en) | 1973-03-06 | 1974-03-05 | PROCESS FOR THE PREPARATION OF NEW 1-AMINO- OR 1-AMINOMETHYL-7,7-DIMETHYL-2,2,1-CYCLO-HEPTANES AND THEIR ACID ADDITION SALTS |
NL7402940A NL7402940A (en) | 1973-03-06 | 1974-03-05 | |
ZA00741433A ZA741433B (en) | 1973-03-06 | 1974-03-05 | Bornane derivatives and processes for their preparation |
LU69557A LU69557A1 (en) | 1973-03-06 | 1974-03-05 | |
AU66280/74A AU493850B2 (en) | 1974-03-05 | Chemical composition | |
US05/555,147 US4087551A (en) | 1973-03-06 | 1975-03-04 | Amino-bicycloheptanes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1089473A GB1468349A (en) | 1973-03-06 | 1973-03-06 | 10-bornanamine and 7,7-dimethyl-norbornan-1-amine and derivatives thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1468349A true GB1468349A (en) | 1977-03-23 |
Family
ID=9976283
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1089473A Expired GB1468349A (en) | 1973-03-06 | 1973-03-06 | 10-bornanamine and 7,7-dimethyl-norbornan-1-amine and derivatives thereof |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE811876A (en) |
GB (1) | GB1468349A (en) |
ZA (1) | ZA741433B (en) |
-
1973
- 1973-03-06 GB GB1089473A patent/GB1468349A/en not_active Expired
-
1974
- 1974-03-05 BE BE141644A patent/BE811876A/en unknown
- 1974-03-05 ZA ZA00741433A patent/ZA741433B/en unknown
Also Published As
Publication number | Publication date |
---|---|
BE811876A (en) | 1974-09-05 |
ZA741433B (en) | 1975-03-26 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |