GB856460A - Carbamic acid derivatives - Google Patents
Carbamic acid derivativesInfo
- Publication number
- GB856460A GB856460A GB23775/58A GB2377558A GB856460A GB 856460 A GB856460 A GB 856460A GB 23775/58 A GB23775/58 A GB 23775/58A GB 2377558 A GB2377558 A GB 2377558A GB 856460 A GB856460 A GB 856460A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- naphthyl
- carbamic acid
- methyl
- substituted
- 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
- 150000004657 carbamic acid derivatives Chemical class 0.000 title 1
- -1 N-(substituted-naphthyl)-carbamic acid Chemical class 0.000 abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001414 amino alcohols Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 150000005002 naphthylamines Chemical class 0.000 abstract 2
- SKUYVURWAOKGNB-UHFFFAOYSA-N 1-[benzyl(methyl)amino]ethanol Chemical compound CC(O)N(C)CC1=CC=CC=C1 SKUYVURWAOKGNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 229910052736 halogen Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises compounds of the formulae: <FORM:0856460/IV(b)/1> (wherein R1 is alkyl, alkoxy or halogen, R2 is alkylene, R3 is hydrogen or alkyl and R4 is alkyl, or R3 and R4 may form, together with the nitrogen atom, a saturated heterocyclic ring which may contain another hetero atom), and their preparation by the following methods-(1) reacting the appropriate substituted naphthylamines with haloformic acid-haloalkyl esters X.COO.R2X (X being a halogen atom) and then condensing the N-(substituted-naphthyl)-carbamic acid-haloalkyl esters so formed with amines NHR3R4; or (2) for compounds wherein R3 is alkyl, reacting the appropriate substituted naphthylamines with haloformic acid-aminoalkyl esters X.COO.R2NR3R4 or reacting the appropriate N-(substituted-naphthyl)-carbamic acid halides or substituted-naphthyl isocyanates with amino-alcohols HO.R2.NR3R4, or by re-esterifying the appropriate N-(substituted naphthyl)-carbamic acid alkyl esters with the same amino-alcohols; or (3) for compounds wherein R3 is hydrogen, debenzylating, by catalytic hydrogenation, the corresponding compounds wherein R3 is benzyl. Examples describe the preparation of the 2-(methylamino)-ethyl, 2-(hexamethyleneimino)-ethyl, 2-(diethylamino)-ethyl, 2-(di-n-butylamino) -ethyl, 2-(dimethylamino)-1-methyl-ethyl, 2-(piperidino)-ethyl and 2-(morpholino)-ethyl esters of 2-methyl-naphthyl-1-carbamic acid, the 2-piperidino)-ethyl ester of 2-ethoxy-naphthyl-1-carbamic acid, the 2-(piperidino)-ethyl and 2-(hexamethyleneimino)-ethyl esters of 2-n-butoxy-naphthyl-1-carbamic acid and of 2-chloronaphthyl-1-carbamic acid and the 2-(piperidino)-ethyl ester of 1-methyl-naphthyl-2-carbamic acid. Hydrochlorides of these products are also described. 2-Methyl-naphthyl-1-carbamic acid-b -( (N-methyl-N-benzylamino)-ethyl ester hydrochloride is prepared from 2-methyl-naphthyl-1-isocyanate and N-methyl-N-benzyl-amino-ethanol and then hydrogen chloride. Specifications 717,211, 717,212, 717,213, 717,214 and 734,745 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE856460X | 1957-07-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB856460A true GB856460A (en) | 1960-12-14 |
Family
ID=6789335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23775/58A Expired GB856460A (en) | 1957-07-25 | 1958-07-23 | Carbamic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB856460A (en) |
-
1958
- 1958-07-23 GB GB23775/58A patent/GB856460A/en not_active Expired
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