CH368802A - Verfahren zur Herstellung von neuen hydroxylierten Indol-Derivaten - Google Patents

Verfahren zur Herstellung von neuen hydroxylierten Indol-Derivaten

Info

Publication number: CH368802A
Authority: CH; Switzerland
Prior art keywords: solution; preparation; indole derivatives; ether; benzyloxy
Prior art date: 1958-09-12

Application number

CH6387458A

Other languages

German (de)

English (en)

Inventor

Albert Dr Hofmann

Franz Dr Troxler

Original Assignee

Sandoz Ag

Priority date (The priority date 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 date listed.)

1958-09-12

Filing date

1958-09-12

Publication date

1963-04-30

1958-09-12 Application filed by Sandoz Ag filed Critical Sandoz Ag

1958-09-12 Priority to CH6387458A priority Critical patent/CH368802A/de

1959-08-13 Priority to ES0251429A priority patent/ES251429A1/es

1959-09-04 Priority to BE582352A priority patent/BE582352A/fr

1960-08-29 Priority to FR837066A priority patent/FR374M/fr

1963-04-30 Publication of CH368802A publication Critical patent/CH368802A/de

1964-12-31 Priority to OA51507A priority patent/OA01260A/fr

Links

150000002475 indoles Chemical class 0.000 title claims description 7
238000000034 method Methods 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
235000006408 oxalic acid Nutrition 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
229910010084 LiAlH4 Inorganic materials 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
RVBHLXCWKWOISZ-UHFFFAOYSA-N 3-(2-piperidin-1-ylethyl)-1h-indol-4-ol Chemical compound C1=2C(O)=CC=CC=2NC=C1CCN1CCCCC1 RVBHLXCWKWOISZ-UHFFFAOYSA-N 0.000 description 2
OHHYMKDBKJPILO-UHFFFAOYSA-N 3-[2-(diethylamino)ethyl]-1h-indol-4-ol Chemical compound C1=CC(O)=C2C(CCN(CC)CC)=CNC2=C1 OHHYMKDBKJPILO-UHFFFAOYSA-N 0.000 description 2
LJFVSIDBFJPKLD-UHFFFAOYSA-N 4-phenylmethoxy-1h-indole Chemical compound C=1C=CC=2NC=CC=2C=1OCC1=CC=CC=C1 LJFVSIDBFJPKLD-UHFFFAOYSA-N 0.000 description 2
PYLMOUWTJKAOFU-UHFFFAOYSA-N 4-phenylmethoxy-3-(2-piperidin-1-ylethyl)-1H-indole Chemical compound C(CC1=CNC2=CC=CC(OCC3=CC=CC=C3)=C12)N1CCCCC1 PYLMOUWTJKAOFU-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 2
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 2
FBICNCYJPHBDGN-UHFFFAOYSA-N n,n-diethyl-2-(4-phenylmethoxy-1h-indol-3-yl)ethanamine Chemical compound C=12C(CCN(CC)CC)=CNC2=CC=CC=1OCC1=CC=CC=C1 FBICNCYJPHBDGN-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
SPCIYGNTAMCTRO-UHFFFAOYSA-N psilocin Chemical compound C1=CC(O)=C2C(CCN(C)C)=CNC2=C1 SPCIYGNTAMCTRO-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
HELUTFGNJXNTCA-UHFFFAOYSA-N 2-(1H-indol-3-yl)-N,N-dimethyl-1-phenylmethoxyethanamine Chemical compound C(C1=CC=CC=C1)OC(N(C)C)CC1=CNC2=CC=CC=C12 HELUTFGNJXNTCA-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229940054051 antipsychotic indole derivative Drugs 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
238000002955 isolation Methods 0.000 description 1
-1 lithium aluminum hydride Chemical compound 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
LHERKDDDEMCCCU-UHFFFAOYSA-N n,n-dimethyl-2-(4-phenylmethoxy-1h-indol-3-yl)ethanamine Chemical compound C=12C(CCN(C)C)=CNC2=CC=CC=1OCC1=CC=CC=C1 LHERKDDDEMCCCU-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)

CH6387458A 1958-09-12 1958-09-12 Verfahren zur Herstellung von neuen hydroxylierten Indol-Derivaten CH368802A (de)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
CH6387458A CH368802A (de)	1958-09-12	1958-09-12	Verfahren zur Herstellung von neuen hydroxylierten Indol-Derivaten
ES0251429A ES251429A1 (es)	1958-09-12	1959-08-13	Procedimiento para la obtenciën de nuevos derivados de indol
BE582352A BE582352A (fr)	1958-09-12	1959-09-04	Procédé de préparation de nouveaux dérivés de l'indole.
FR837066A FR374M (fr)	1958-09-12	1960-08-29	Médicament a base de dérivé de la tryptamine.
OA51507A OA01260A (fr)	1958-09-12	1964-12-31	Procédé de préparation de nouveaux dérivés de l'indole.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH6387458A CH368802A (de)	1958-09-12	1958-09-12	Verfahren zur Herstellung von neuen hydroxylierten Indol-Derivaten

Publications (1)

Publication Number	Publication Date
CH368802A true CH368802A (de)	1963-04-30

Family

ID=4525271

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6387458A CH368802A (de)	1958-09-12	1958-09-12	Verfahren zur Herstellung von neuen hydroxylierten Indol-Derivaten

Country Status (2)

Country	Link
BE (1)	BE582352A (fr)
CH (1)	CH368802A (fr)

1958
- 1958-09-12 CH CH6387458A patent/CH368802A/de unknown
1959
- 1959-09-04 BE BE582352A patent/BE582352A/fr unknown

Also Published As

Publication number	Publication date
BE582352A (fr)	1960-03-04

Publication	Publication Date	Title
DE1961778A1 (de)	1970-06-18	Verfahren zur Herstellung von Brenzcatechin-Derivaten
DE2933636A1 (de)	1980-03-20	Neue n-phenylindolinderivate, ihre herstellung und pharmazeutische praeparate, welche diese verbindungen enthalten
CH368802A (de)	1963-04-30	Verfahren zur Herstellung von neuen hydroxylierten Indol-Derivaten
AT213885B (de)	1961-03-10	Verfahren zur Herstellung von neuen Indol-Derivaten
DE745314C (de)	1944-11-27	Verfahren zur Herstellung von analgetisch wirkenden 1-Oxyphenyl-3-aminoalkylverbindungen
NO133067B (fr)	1975-11-24
AT371445B (de)	1983-06-27	Verfahren zur herstellung von neuen cis-4a-phenyl-isochinolinderivaten und ihren saeureadditionssalzen
US2498433A (en)	1950-02-21	1,3 dimethyl-4-propionoxy-4-phenyl-piperidine and acid addition salts thereof
DE2148552A1 (de)	1972-04-06	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
DE1543359C (fr)	1973-05-24
DE1595903C (de)	1972-10-05	1-Substituierte 2,6-Dimethyl-4-phenylpiperazine
AT228218B (de)	1963-07-10	Verfahren zur Herstellung von neuen Thioxanthen-Verbindungen
AT227690B (de)	1963-06-10	Verfahren zur Herstellung neuer, basisch substituierter Succinimide
AT210435B (de)	1960-08-10	Verfahren zur Herstellung von neuen Ferrocenderivaten
CH375712A (de)	1964-03-15	Verfahren zur Herstellung von neuen, hydroxylierten Indol-Derivaten
AT214928B (de)	1961-05-10	Verfahren zur Herstellung von neuen Camphidiniumverbindungen
CH526544A (de)	1972-08-15	Verfahren zur Herstellung neuer Indolderivate
AT233570B (de)	1964-05-11	Verfahren zur Herstellung von neuen N-Phenylpiperazinderivaten
AT218520B (de)	1961-12-11	Verfahren zur Herstellung von neuen Piperidin- und Tetrahydropyridinderivaten
AT238181B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
AT239255B (de)	1965-03-25	Verfahren zur Herstellung von neuen basisch substituierten Alkylxanthinderivaten
DE2506515A1 (de)	1975-09-11	Verfahren zur herstellung von 2-aminomethylpyrrolidin
DE1098510B (de)	1961-02-02	Verfahren zur Herstellung von 3-substituierten 1-Benzylindanen
CH530397A (de)	1972-11-15	Verfahren zur Herstellung neuer Indolderivate
DE1156077B (de)	1963-10-24	Verfahren zur Herstellung von 4-Hydroxytryptaminderivaten und deren Salzen