SU383369A1 - Способ получени хлоргидрата -метил-1адамантилметиламина - Google Patents
Способ получени хлоргидрата -метил-1адамантилметиламинаInfo
- Publication number
- SU383369A1 SU383369A1 SU1641577A SU1641577A SU383369A1 SU 383369 A1 SU383369 A1 SU 383369A1 SU 1641577 A SU1641577 A SU 1641577A SU 1641577 A SU1641577 A SU 1641577A SU 383369 A1 SU383369 A1 SU 383369A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- preparing
- hydrochloride
- mixture
- methylmethyl
- acetamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- NZXLSJFSECATQY-UHFFFAOYSA-N Cl.CN(C)CC12CC3CC(CC(C1)C3)C2 Chemical compound Cl.CN(C)CC12CC3CC(CC(C1)C3)C2 NZXLSJFSECATQY-UHFFFAOYSA-N 0.000 title 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- DACIGVIOAFXPHW-UHFFFAOYSA-N 1-(1-adamantyl)ethanone Chemical compound C1C(C2)CC3CC2CC1(C(=O)C)C3 DACIGVIOAFXPHW-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 2
- DQSIEXZABIATEF-UHFFFAOYSA-N 1-(1-adamantyl)-n-methylmethanamine Chemical group C1C(C2)CC3CC2CC1(CNC)C3 DQSIEXZABIATEF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- RGWHHWWMFUXNAX-UHFFFAOYSA-N bis(1-adamantyl)methanone Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)C1(C2)CC(C3)CC2CC3C1 RGWHHWWMFUXNAX-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940052761 dopaminergic adamantane derivative Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/38—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/28—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with other reducing agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
-
- 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
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1641577A SU383369A1 (ru) | 1971-04-13 | 1971-04-13 | Способ получени хлоргидрата -метил-1адамантилметиламина |
| US00214381A US3852352A (en) | 1971-04-13 | 1971-12-30 | Method of producing alpha-methyl-1-adamantylmethyl-amine hydrochloride |
| DE2200939A DE2200939C3 (de) | 1971-04-13 | 1972-01-10 | Verfahren zur Herstellung von Hl'-Aminoäthyl)adamantanhydrochlorid |
| FR7202562A FR2132627B1 (OSRAM) | 1971-04-13 | 1972-01-26 | |
| CH545472A CH576421A5 (OSRAM) | 1971-04-13 | 1972-04-13 | |
| BE782052A BE782052A (fr) | 1969-12-12 | 1972-04-13 | Procede de preparation de chlorhydrate de alpha-methyl-1-adamanthylmethylamine et produit obtenu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1641577A SU383369A1 (ru) | 1971-04-13 | 1971-04-13 | Способ получени хлоргидрата -метил-1адамантилметиламина |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU383369A1 true SU383369A1 (ru) | 1976-12-25 |
Family
ID=20470979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1641577A SU383369A1 (ru) | 1969-12-12 | 1971-04-13 | Способ получени хлоргидрата -метил-1адамантилметиламина |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3852352A (OSRAM) |
| CH (1) | CH576421A5 (OSRAM) |
| DE (1) | DE2200939C3 (OSRAM) |
| FR (1) | FR2132627B1 (OSRAM) |
| SU (1) | SU383369A1 (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2635991C2 (ru) * | 2016-03-18 | 2017-11-17 | Открытое акционерное общество "Ирбитский химико-фармацевтический завод" | Способ получения римантадина гидрохлорида |
| US11608313B2 (en) | 2017-08-02 | 2023-03-21 | Tohoku University | Adamantylmethylamine derivative and use thereof as pharmaceutical |
-
1971
- 1971-04-13 SU SU1641577A patent/SU383369A1/ru active
- 1971-12-30 US US00214381A patent/US3852352A/en not_active Expired - Lifetime
-
1972
- 1972-01-10 DE DE2200939A patent/DE2200939C3/de not_active Expired
- 1972-01-26 FR FR7202562A patent/FR2132627B1/fr not_active Expired
- 1972-04-13 CH CH545472A patent/CH576421A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2200939A1 (de) | 1972-10-19 |
| FR2132627B1 (OSRAM) | 1975-10-10 |
| DE2200939C3 (de) | 1979-03-22 |
| CH576421A5 (OSRAM) | 1976-06-15 |
| FR2132627A1 (OSRAM) | 1972-11-24 |
| US3852352A (en) | 1974-12-03 |
| DE2200939B2 (de) | 1978-07-20 |
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