ES306773A1 - Procedure for the preparation of i - aminoadamantane. (Machine-translation by Google Translate, not legally binding) - Google Patents
Procedure for the preparation of i - aminoadamantane. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES306773A1 ES306773A1 ES0306773A ES306773A ES306773A1 ES 306773 A1 ES306773 A1 ES 306773A1 ES 0306773 A ES0306773 A ES 0306773A ES 306773 A ES306773 A ES 306773A ES 306773 A1 ES306773 A1 ES 306773A1
- Authority
- ES
- Spain
- Prior art keywords
- aminoadamantane
- preparation
- water
- trimethylenic
- solvent
- 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
- 238000002360 preparation method Methods 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 5
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- -1 1-substituted adamantane Chemical class 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000007900 aqueous suspension Substances 0.000 abstract 2
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- VQHPRVYDKRESCL-UHFFFAOYSA-N 1-bromoadamantane Chemical class C1C(C2)CC3CC2CC1(Br)C3 VQHPRVYDKRESCL-UHFFFAOYSA-N 0.000 abstract 1
- 238000006434 Ritter amidation reaction Methods 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 238000012423 maintenance Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000012264 purified product Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/605—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system
- C07C13/615—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system with an adamantane ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/29—Rearrangement of carbon atoms in the hydrocarbon skeleton changing the number of carbon atoms in a ring while maintaining the number of rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
- C07C2603/68—Dicyclopentadienes; Hydrogenated dicyclopentadienes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Preparation process of 1-aminoadamantane, comprising the isomerization of trimethylenic norbornane with Cl3Al and C1H maintaining the process conditions at atmospheric pressure and at 90-120º C for 1 to 4 hours while stirring norbornene trimethylenic with 0.1 to 0.3 mol of hydrochloric acid and 0.4 to 0.6 mol of aluminum chloride per mole of trimethylenic norbornane. 2a.) Bromination of said adamantane. 2b.) Subjection of this 1-bromoadamantane to the Ritter reaction with acetonitrile and sulfuric acid. 2c.) Hydrolyzing this product or, as a variant, 2aa.) Preparation of a 1-substituted adamantane with a "remaining group" in said position 1. 2bb.) Heating under pressure of this 1-substituted adamantane, in which the substitute in position 1 is a remaining group, with ammonia, at the level of 80 to 325º C 3.) Purification of said 1-aminoadamantane, comprising: A ) The codestylation of an aqueous suspension of crude 1-aminoadamantane with water; B) Condensation of the vapors produced in operation A; C) Maintenance of the resulting condensate at 60ºC-120ºC until it has left the condenser; and D) Separation of the purified product. 4.) Optionally, the preparation of 1-aminoadamantane hydrochloride, comprising: A) The co-distillation of an aqueous suspension of crude 1-aminoadamantane with water; B) The extraction of the free amine from the distillate with water vapor cooled, with an organic solvent, low boiling and unmixable with water, said solvent being inert with respect to hydrochloric acid and not reactive with amine; C) The mixture of the resulting 1-aminoadamantane solution with a slight excess of the stoichiometrically equivalent amount of anhydrous hydrogen chloride; and D) The separation of the 1-aminoadamantane hydrochloride formed from the solvent. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33195663A | 1963-12-19 | 1963-12-19 | |
| US365134A US3283001A (en) | 1961-10-26 | 1964-05-05 | 1-aminoadamantane and process for purifying same |
| US373825A US3256329A (en) | 1961-10-26 | 1964-06-09 | Process for preparing bridgehead-substituted bicyclo [2. 2. 2] octane and tricyclo [3. 3. 1. 13, 7] decane amines and diamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES306773A1 true ES306773A1 (en) | 1965-04-16 |
Family
ID=27406831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0306773A Expired ES306773A1 (en) | 1963-12-19 | 1964-12-04 | Procedure for the preparation of i - aminoadamantane. (Machine-translation by Google Translate, not legally binding) |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES306773A1 (en) |
| OA (1) | OA00993A (en) |
-
1964
- 1964-12-04 ES ES0306773A patent/ES306773A1/en not_active Expired
- 1964-12-29 OA OA51096A patent/OA00993A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| OA00993A (en) | 1968-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3876715A (en) | Process for preparing 2,3-dibromo-2-alkylalkanes | |
| GB1037255A (en) | Process and apparatus for the continuous distillation of mixtures | |
| GB1066954A (en) | Separation of ammonia from aqueous solutions | |
| ES407225A1 (en) | Secondary removal of inerts in ethylene oxide purification | |
| GB1122609A (en) | Production of a mixture of stereoisomers of 4,4'-methylenedi(cyclohexylamine) | |
| US2509859A (en) | Nitriles from butadiene and hydrogen cyanide | |
| US3131132A (en) | Purification of dimethylaminoethanol by acid treatment and distillation | |
| US2844589A (en) | Process for the preparation of belta2-oxazoline | |
| GB998639A (en) | Improvements in or relating to the purification of acrylonitrile by distillation | |
| McKay et al. | levo-2, 3-Dinitroxybutane | |
| US4003924A (en) | Process for preparing 1-amino anthraquinone | |
| GB422563A (en) | Improvements in the manufacture and production of aliphatic amines | |
| US2550020A (en) | Manufacture of primary amines | |
| GB1452904A (en) | Purification of adiponitrile | |
| GB1028225A (en) | Separation of isobutyl alcohol and isobutyronitrile from mixtures thereof by azeotropic distillation | |
| GB743306A (en) | Purification of acrylonitrile by distillation | |
| GB923463A (en) | Recovery of hexamethylphosphorictriamide | |
| Ellzey Jr et al. | Reduction of Polyfluoroalkyl Nitriles with Sodium Borohydride | |
| US2105828A (en) | Production of morpholine ethanols | |
| SU292474A1 (en) | Process for preparing 1-naphthylamine | |
| US2837567A (en) | Preparation of beta, beta'-oxydipropionic acid | |
| US3781362A (en) | Removal of 1,2-diaminocyclohexane impurity from crude hexamethylenediamine | |
| US3391215A (en) | Preparation of isoprene | |
| GB675777A (en) | Improvements in and relating to the rectification of methylchlorosilanes | |
| Woodburn et al. | THE REACTION OF CYANOGEN WITH ORGANIC COMPOUNDS. III. SUBSTITUTION AND EXCHANGE REACTIONS OF DIALKYLOXAMIDINES1, 2 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19840223 |