SU562192A3 - The method of obtaining-methyl- (3,4,5-trimethoxybenzyl) -2,3 dimethyl-2,4-pentadienamine or its salts - Google Patents
The method of obtaining-methyl- (3,4,5-trimethoxybenzyl) -2,3 dimethyl-2,4-pentadienamine or its saltsInfo
- Publication number
- SU562192A3 SU562192A3 SU2129803A SU2129803A SU562192A3 SU 562192 A3 SU562192 A3 SU 562192A3 SU 2129803 A SU2129803 A SU 2129803A SU 2129803 A SU2129803 A SU 2129803A SU 562192 A3 SU562192 A3 SU 562192A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- salt
- trimethoxybenzyl
- dimethyl
- formula
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 4
- 150000003839 salts Chemical class 0.000 title claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- BETAQCRRCJRXRB-UHFFFAOYSA-M 1,4,5-trimethyl-1-[(3,4,5-trimethoxyphenyl)methyl]-3,6-dihydro-2h-pyridin-1-ium;chloride Chemical compound [Cl-].COC1=C(OC)C(OC)=CC(C[N+]2(C)CC(C)=C(C)CC2)=C1 BETAQCRRCJRXRB-UHFFFAOYSA-M 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- -1 hydrochloric acid amine salt Chemical class 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
- 239000012044 organic layer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Полученный осадок фильтруют, иромываJoT смесью ацетон : эфир (1:1) и выдел ют 79 г соединени формулы П. Выход 92%. Т. пл. 149-152°С (ацетон - абсолютный спирт).The resulting precipitate was filtered and washed with a mixture of acetone: ether (1: 1) and 79 g of compound of the formula P was isolated. Yield 92%. T. pl. 149-152 ° C (acetone - absolute alcohol).
Найдено, %: С 59,90; Н 8,38; N 3,85.Found,%: C 59.90; H 8.38; N 3.85.
CisHssNOsCl НгО.CisHssNOsCl HgO.
Вычислено, %: С 60,08; Н 8,40; N 3,89.Calculated,%: C 60.08; H 8.40; N 3.89.
Пример 2. Получение Ы-метил-М- (3,4,5триметоксибензил ) - 2,3- димeтил-2,4-пeнтaдиенамина (I) и его гидрохлорида.Example 2. Preparation of N-methyl-M- (3,4,5trimethoxybenzyl) -2,3-dimethyl-2,4-pentadiene amine (I) and its hydrochloride.
16,2 г 1,3,4-триметил-1- (3,4,5-триметоксибензил ) -1,2,5,6-тетра;гидропи1ридина хлористого (П), 25,2 г гидроокиси кали и 145 мл воды нагревают при температуре кипени в течение 33 ч и наблюдают отделение оргалического сло .16.2 g of 1,3,4-trimethyl-1- (3,4,5-trimethoxybenzyl) -1,2,5,6-tetra; hydropyridine chloride (P), 25.2 g of potassium hydroxide and 145 ml of water The mixture is heated at boiling point for 33 hours and the separation of the organic layer is observed.
Полученный амин экстрагируют эфиром, эфирный слой высушивают над сульфатом «атри и по капл ад прибавл ют эфирный раствор хлористого водорода до кислой среды. Выдавшую в осадок сол нокиснуюсоль амина формулы I фильтруют. Выход 9 г. Т. пл. 202-204°С.The resulting amine is extracted with ether, the ether layer is dried over atrium sulphate and ethereal hydrogen chloride solution is added dropwise to the acidic medium. The precipitated hydrochloric acid amine salt of formula I is filtered. Exit 9 g. T. pl. 202-204 ° C.
Из оставшегос водного сло после дополнительного нагревани в течение 45 ч, с последующей выше описанной обработкой выдел ют дополнительно 2,1 г сол о.кислой соли амииа формулы J. Суммарный выход продукта 72%.After additional heating for 45 hours from the remaining aqueous layer, followed by the treatment described above, an additional 2.1 g of the ammonium hydrochloride salt of formula J. were isolated. The total yield of the product was 72%.
Найдено, %: С 63,09; Н 8,27; N 4,12.Found,%: C 63.09; H 8.27; N 4.12.
CisHzsNOsCl.CisHzsNOsCl.
Вычислено, %: С 63,24; Н 8,25; N 4,09.Calculated,%: C 63.24; H 8.25; N 4.09.
Формула и 3 о б р е т е .Н и Formula and 3 abbet e .N and
Claims (3)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES425970A ES425970A1 (en) | 1974-05-04 | 1974-05-04 | Pharmaceutically active amines |
Publications (1)
Publication Number | Publication Date |
---|---|
SU562192A3 true SU562192A3 (en) | 1977-06-15 |
Family
ID=8466594
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU2129803A SU562192A3 (en) | 1974-05-04 | 1975-05-04 | The method of obtaining-methyl- (3,4,5-trimethoxybenzyl) -2,3 dimethyl-2,4-pentadienamine or its salts |
Country Status (14)
Country | Link |
---|---|
JP (1) | JPS5337337B2 (en) |
AR (1) | AR206623A1 (en) |
AT (1) | AT337160B (en) |
AU (1) | AU8050775A (en) |
BE (1) | BE828240A (en) |
CA (1) | CA1052794A (en) |
CH (1) | CH615150A5 (en) |
DE (1) | DE2518534A1 (en) |
ES (1) | ES425970A1 (en) |
FR (1) | FR2269336B1 (en) |
GB (1) | GB1501153A (en) |
NL (1) | NL7505254A (en) |
SE (1) | SE412755B (en) |
SU (1) | SU562192A3 (en) |
-
1974
- 1974-05-04 ES ES425970A patent/ES425970A1/en not_active Expired
-
1975
- 1975-01-01 AR AR257859A patent/AR206623A1/en active
- 1975-03-07 AT AT181075A patent/AT337160B/en not_active IP Right Cessation
- 1975-04-15 SE SE7504301A patent/SE412755B/en unknown
- 1975-04-15 GB GB15514/75A patent/GB1501153A/en not_active Expired
- 1975-04-22 BE BE155654A patent/BE828240A/en unknown
- 1975-04-24 AU AU80507/75A patent/AU8050775A/en not_active Expired
- 1975-04-25 DE DE19752518534 patent/DE2518534A1/en active Pending
- 1975-04-30 FR FR7513536A patent/FR2269336B1/fr not_active Expired
- 1975-05-01 CA CA226,057A patent/CA1052794A/en not_active Expired
- 1975-05-02 NL NL7505254A patent/NL7505254A/en not_active Application Discontinuation
- 1975-05-02 CH CH568075A patent/CH615150A5/en not_active IP Right Cessation
- 1975-05-02 JP JP5380075A patent/JPS5337337B2/ja not_active Expired
- 1975-05-04 SU SU2129803A patent/SU562192A3/en active
Also Published As
Publication number | Publication date |
---|---|
AU8050775A (en) | 1976-10-28 |
FR2269336A1 (en) | 1975-11-28 |
AR206623A1 (en) | 1976-08-06 |
CA1052794A (en) | 1979-04-17 |
JPS5337337B2 (en) | 1978-10-07 |
ATA181075A (en) | 1976-10-15 |
CH615150A5 (en) | 1980-01-15 |
BE828240A (en) | 1975-10-22 |
GB1501153A (en) | 1978-02-15 |
SE412755B (en) | 1980-03-17 |
AT337160B (en) | 1977-06-10 |
FR2269336B1 (en) | 1977-09-09 |
DE2518534A1 (en) | 1975-11-13 |
ES425970A1 (en) | 1976-09-16 |
SE7504301L (en) | 1975-11-05 |
NL7505254A (en) | 1975-11-06 |
JPS50151835A (en) | 1975-12-06 |
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