SU453837A3 - Способ получения производныхтетрагидроизохинолина или их кислотно-аддитивных солеи - Google Patents
Способ получения производныхтетрагидроизохинолина или их кислотно-аддитивных солеиInfo
- Publication number
- SU453837A3 SU453837A3 SU1721026A SU1721026A SU453837A3 SU 453837 A3 SU453837 A3 SU 453837A3 SU 1721026 A SU1721026 A SU 1721026A SU 1721026 A SU1721026 A SU 1721026A SU 453837 A3 SU453837 A3 SU 453837A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- dimethoxy
- hydrochloride
- tetrahydroisoquinoline
- acid
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 8
- 239000000654 additive Substances 0.000 title claims description 3
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 title description 4
- -1 trimethylene, tetramethylene Chemical group 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical class C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 229930040373 Paraformaldehyde Natural products 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229920002866 paraformaldehyde Polymers 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 8
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QOODAXYFBLKEBJ-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-4-methylpentan-1-one Chemical compound CC(C)CCC(=O)C1=CC=C(C)C(C)=C1 QOODAXYFBLKEBJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000021736 acetylation Effects 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- NNMCIEOCSPLKDD-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-3-methylbutan-1-one Chemical compound CC(C)CC(=O)C1=CC=C(C)C(C)=C1 NNMCIEOCSPLKDD-UHFFFAOYSA-N 0.000 description 2
- GIOAXJKFXSSPIC-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)octan-1-one Chemical compound CCCCCCCC(=O)C1=CC=C(C)C(C)=C1 GIOAXJKFXSSPIC-UHFFFAOYSA-N 0.000 description 2
- WFJNOVPQFVHWCS-UHFFFAOYSA-N 1-(5,6,7,8-tetrahydronaphthalen-2-yl)butan-1-one Chemical compound C1CCCC2=CC(C(=O)CCC)=CC=C21 WFJNOVPQFVHWCS-UHFFFAOYSA-N 0.000 description 2
- SVWCVXFHTHCJJB-UHFFFAOYSA-N 4-methylpentanoyl chloride Chemical compound CC(C)CCC(Cl)=O SVWCVXFHTHCJJB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011928 denatured alcohol Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- JHPNCOPOHRZANL-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-5-yl)-4-methylpentan-1-one Chemical compound CC(C)CCC(=O)C1=CC=C2CCCC2=C1 JHPNCOPOHRZANL-UHFFFAOYSA-N 0.000 description 1
- WBAYOHQUOKPYOS-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)hexan-1-one Chemical compound CCCCCC(=O)C1=CC=C(C)C(C)=C1 WBAYOHQUOKPYOS-UHFFFAOYSA-N 0.000 description 1
- HTXWKZDRDRFVHN-UHFFFAOYSA-N 2-methyloxiran-2-ol Chemical compound CC1(O)CO1 HTXWKZDRDRFVHN-UHFFFAOYSA-N 0.000 description 1
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
- UJXLTDHDLUBZBL-UHFFFAOYSA-N 6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium;chloride Chemical compound [Cl-].C1C[NH2+]C(C)C2=C1C=C(OC)C(OC)=C2 UJXLTDHDLUBZBL-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- HMYJLVDKPJHJCF-UHFFFAOYSA-N salsolidine hydrochloride Natural products C1CNC(C)C2=C1C=C(OC)C(OC)=C2 HMYJLVDKPJHJCF-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/788—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with keto groups bound to a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5670270 | 1970-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU453837A3 true SU453837A3 (ru) | 1974-12-15 |
Family
ID=10477318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1721026A SU453837A3 (ru) | 1970-11-30 | 1971-11-30 | Способ получения производныхтетрагидроизохинолина или их кислотно-аддитивных солеи |
Country Status (24)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2327689C2 (ru) * | 2003-03-03 | 2008-06-27 | Ф.Хоффманн-Ля Рош Аг | 2,5- замещенные тетрагидроизохинолины и фармацевтическая композиция для модуляции 5-нт6 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4766131A (en) * | 1980-10-17 | 1988-08-23 | Pennwalt Corporation | 2-amino (or hydroxy) phenethyl-1,2,3,4-tetrahydroisoquinolines as analgesics |
-
1970
- 1970-11-30 GB GB5670270A patent/GB1313017A/en not_active Expired
-
1971
- 1971-11-01 EG EG480/71A patent/EG10512A/xx active
- 1971-11-01 ZA ZA717308A patent/ZA717308B/xx unknown
- 1971-11-02 IL IL38066A patent/IL38066A0/xx unknown
- 1971-11-03 AU AU35297/71A patent/AU454027B2/en not_active Expired
- 1971-11-05 CH CH1612571A patent/CH559725A5/xx not_active IP Right Cessation
- 1971-11-11 DE DE19712156049 patent/DE2156049A1/de active Pending
- 1971-11-19 BR BR7706/71A patent/BR7107706D0/pt unknown
- 1971-11-22 US US00203100A patent/US3812133A/en not_active Expired - Lifetime
- 1971-11-23 CS CS8160A patent/CS164916B2/cs unknown
- 1971-11-24 RO RO68853A patent/RO60141A/ro unknown
- 1971-11-26 DD DD159187A patent/DD95232A5/xx unknown
- 1971-11-26 NL NL7116272A patent/NL7116272A/xx unknown
- 1971-11-27 BG BG019118A patent/BG20355A3/xx unknown
- 1971-11-29 AT AT1024271A patent/AT317215B/de not_active IP Right Cessation
- 1971-11-29 ES ES397454A patent/ES397454A1/es not_active Expired
- 1971-11-29 SE SE7115274A patent/SE374110B/xx unknown
- 1971-11-29 DK DK583771AA patent/DK129236B/da unknown
- 1971-11-29 BE BE775949A patent/BE775949A/xx unknown
- 1971-11-30 SU SU1721026A patent/SU453837A3/ru active
- 1971-11-30 FR FR7142902A patent/FR2115493B1/fr not_active Expired
- 1971-11-30 HU HUHO1436A patent/HU162419B/hu unknown
- 1971-11-30 FI FI713419A patent/FI49605C/fi active
-
1974
- 1974-12-31 MY MY197444A patent/MY7400044A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2327689C2 (ru) * | 2003-03-03 | 2008-06-27 | Ф.Хоффманн-Ля Рош Аг | 2,5- замещенные тетрагидроизохинолины и фармацевтическая композиция для модуляции 5-нт6 |
Also Published As
| Publication number | Publication date |
|---|---|
| EG10512A (en) | 1976-03-31 |
| FI49605B (enrdf_load_html_response) | 1975-04-30 |
| GB1313017A (en) | 1973-04-11 |
| FR2115493A1 (enrdf_load_html_response) | 1972-07-07 |
| US3812133A (en) | 1974-05-21 |
| FI49605C (fi) | 1975-08-11 |
| RO60141A (enrdf_load_html_response) | 1976-07-15 |
| AT317215B (de) | 1974-08-26 |
| BE775949A (fr) | 1972-05-29 |
| IL38066A0 (en) | 1972-01-27 |
| HU162419B (enrdf_load_html_response) | 1973-02-28 |
| NL7116272A (enrdf_load_html_response) | 1972-06-01 |
| MY7400044A (en) | 1974-12-31 |
| SE374110B (enrdf_load_html_response) | 1975-02-24 |
| FR2115493B1 (enrdf_load_html_response) | 1974-11-15 |
| ZA717308B (en) | 1972-11-29 |
| DD95232A5 (enrdf_load_html_response) | 1973-01-20 |
| CS164916B2 (enrdf_load_html_response) | 1975-11-28 |
| CH559725A5 (enrdf_load_html_response) | 1975-03-14 |
| BR7107706D0 (pt) | 1973-07-12 |
| AU454027B2 (en) | 1974-10-17 |
| DE2156049A1 (de) | 1972-06-08 |
| AU3529771A (en) | 1973-05-10 |
| DK129236B (da) | 1974-09-16 |
| DK129236C (enrdf_load_html_response) | 1975-02-03 |
| ES397454A1 (es) | 1974-06-01 |
| BG20355A3 (bg) | 1975-11-05 |
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