NO133068B - - Google Patents
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- Publication number
- NO133068B NO133068B NO305370A NO305370A NO133068B NO 133068 B NO133068 B NO 133068B NO 305370 A NO305370 A NO 305370A NO 305370 A NO305370 A NO 305370A NO 133068 B NO133068 B NO 133068B
- Authority
- NO
- Norway
- Prior art keywords
- phosphoric acid
- hydroxy
- acid ester
- indole
- dibenzyl
- Prior art date
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- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 6
- 150000002475 indoles Chemical class 0.000 claims description 6
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- -1 lithium aluminum hydride Chemical compound 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- SMVXYBYTGKEHCS-UHFFFAOYSA-N [benzyl(chloro)phosphoryl]methylbenzene Chemical compound C=1C=CC=CC=1CP(=O)(Cl)CC1=CC=CC=C1 SMVXYBYTGKEHCS-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- HDFFVHSMHLDSLO-UHFFFAOYSA-N Dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)(O)OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BCBIDTUKRGWHPL-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-1h-indol-4-ol;phosphoric acid Chemical compound OP(O)(O)=O.C1=CC(O)=C2C(CCN(C)C)=CNC2=C1 BCBIDTUKRGWHPL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-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
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 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
- 230000001624 sedative effect Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QTERVOZQCNPERI-UHFFFAOYSA-N 1h-indole;phosphoric acid Chemical compound OP(O)(O)=O.C1=CC=C2NC=CC2=C1 QTERVOZQCNPERI-UHFFFAOYSA-N 0.000 description 1
- KSDRYRLZDHZMDM-UHFFFAOYSA-N 2-(4-phenylmethoxy-1h-indol-3-yl)ethanamine Chemical compound C=12C(CCN)=CNC2=CC=CC=1OCC1=CC=CC=C1 KSDRYRLZDHZMDM-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 244000172533 Viola sororia Species 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000011083 clear filtration Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01F—PROCESSING OF HARVESTED PRODUCE; HAY OR STRAW PRESSES; DEVICES FOR STORING AGRICULTURAL OR HORTICULTURAL PRODUCE
- A01F25/00—Storing agricultural or horticultural produce; Hanging-up harvested fruit
- A01F25/04—Stacks, ricks or the like
- A01F25/045—Distributing arrangements in haystacks
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65G—TRANSPORT OR STORAGE DEVICES, e.g. CONVEYORS FOR LOADING OR TIPPING, SHOP CONVEYOR SYSTEMS OR PNEUMATIC TUBE CONVEYORS
- B65G53/00—Conveying materials in bulk through troughs, pipes or tubes by floating the materials or by flow of gas, liquid or foam
- B65G53/34—Details
- B65G53/52—Adaptations of pipes or tubes
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Cleaning In General (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
- Specific Conveyance Elements (AREA)
- Indole Compounds (AREA)
- Feeding And Watering For Cattle Raising And Animal Husbandry (AREA)
Description
Fremgangsmåte for fremstilling av nye, fosforholdige indolderivater. Process for the production of new phosphorus-containing indole derivatives.
Det har vist seg at det er mulig å It has been shown that it is possible to
komme frem til nye, fosforholdige indolderivater med den alminnelige formel I arrive at new phosphorus-containing indole derivatives with the general formula I
hvor R, og R, betyr like eller forskjellige where R, and R, mean the same or different
alkylgrupper med 1—4 kullstoffatomer eller sammen med nitrogenatomet en piperi-dinring, ved at et 4-hydroksy-indol-derivat alkyl groups with 1-4 carbon atoms or together with the nitrogen atom a piperidine ring, in that a 4-hydroxy-indole derivative
med den alminnelige formel II with the general formula II
hvor R, og Ro har samme betydning som where R, and Ro have the same meaning as
ovenfor, i form av sitt salt med en anor-ganisk base i et inert oppløsningsmiddel above, in the form of its salt with an inorganic base in an inert solvent
overføres til fosforsyreesteren ved å be-handles med reaksjonsdyktige derivater av is transferred to the phosphoric acid ester by treatment with reactive derivatives of
fosforsyre. phosphoric acid.
De nye, fosforholdige indolderivater utmerker seg ved interessante terapeutisk brukbare farmakodynamiske egenskaper. De bevirker spesielt en stimulering av det sentrale sympatiske nervesystem, som yt-rer seg i mydriase, blodtrykkstigning, temperaturøkning og blodsukkerøking. Videre The new phosphorus-containing indole derivatives are distinguished by interesting therapeutically useful pharmacodynamic properties. They cause in particular a stimulation of the central sympathetic nervous system, which manifests itself in mydriasis, rise in blood pressure, rise in temperature and rise in blood sugar. Further
befordrer de spinale reflekser. Samtidig promotes the spinal reflexes. Simultaneous
virker stoffene i liten grad beroligende og driftshemmende. På grunn av sine sentralt vegetative og sine driftshemmende og se-dative egenskaper kan de anvendes for the substances are to a small extent sedating and work-inhibiting. Because of their centrally vegetative and their inhibitory and sedative properties, they can be used for
behandling av de forskjelligste psykiske sykdommer, først og fremst tvangsneuro-ser samt depresjoner, forstemthet og treatment of a wide variety of mental illnesses, primarily obsessive-compulsive disorders as well as depression, moodiness and
angsttilstander av neurotisk og psykotisk art. De fosforholdige indolderivater med formel I har en meget liten giftighet. De anxiety states of a neurotic and psychotic nature. The phosphorus-containing indole derivatives of formula I have very little toxicity. The
resorberes praktisk talt kvantitativt av or-ganismen og kommer derfor fortrinnsvis til bruk peroralt, men kan like godt tas inn is absorbed practically quantitatively by the body and is therefore preferably used orally, but can just as easily be taken
under huden, i musklene eller i samle-årene. De skal benyttes i terapien. under the skin, in the muscles or in the veins. They must be used in therapy.
De nye forbindelser er meget svakt oppløselige i nesten alle organiske oppløs-ningsmidler, men derimot forholdsvis lett i vann. Med Keller-reagens (iseddik som inneholder jern-III-klorid og kons svovel-syre) gir de en positiv farvereaksjon. The new compounds are very slightly soluble in almost all organic solvents, but relatively easily in water. With Keller's reagent (glacial vinegar containing ferric chloride and concentrated sulfuric acid) they give a positive color reaction.
De indolderivater med formel II som ved fremgangsmåten i henhold til oppfinnelsen benyttes som utgangsmaterial kan fremstilles på følgende måte: 4-benzyloksy-indol oppløses i eter og oppløsningen blir ved lav temperatur først blandet med oksalylklorid og deretter med et lavere dialkylamin eller piperidin. Det derved oppnådde substituerte [4-benzyloksy-indolyl- (3) ] -glykolsyre-dimetyl-amid blir redusert med litium-aluminium-hydrid i abs. dioksan, hvorved det oppnås et 4-benzyloksy-tryptamin som er substi-tuert på sidekjedens nitrogenatom. For av-spalting av benzylgruppen blir tryptamin-derivatet rystet i metanoloppløsning med en palladiumkatalysator i en hydrogen-atmosfære. Etter avsluttet hydrogenopp-tagelse renses forbindelsen, f. eks. ved sub-limering i vakuum eller ved krystallisering. The indole derivatives of formula II which are used as starting material in the process according to the invention can be prepared in the following way: 4-benzyloxy-indole is dissolved in ether and the solution is mixed at low temperature first with oxalyl chloride and then with a lower dialkylamine or piperidine. The thus obtained substituted [4-benzyloxy-indolyl-(3)]-glycolic acid dimethyl-amide is reduced with lithium aluminum hydride in abs. dioxane, whereby a 4-benzyloxy-tryptamine is obtained which is substituted on the nitrogen atom of the side chain. To split off the benzyl group, the tryptamine derivative is shaken in methanol solution with a palladium catalyst in a hydrogen atmosphere. After completion of hydrogen uptake, the compound is purified, e.g. by sublimation in vacuum or by crystallization.
Fremgangsmåten kan eksempelvis ut-føres på følgende måte: Eksempelvis et 4-hydroksy-indolderi-vat med formel II i form av alkalisaltet omsettes med 1 mol dibenzylfosforylklorid 1 et inert oppløsningsmiddel, f. eks. toluol, dimetoksy-etan, tert. amylalkohol o. a., hvoretter oppløsningen blir rystet eller får stå i noen timer ved romtemperatur, even-tuelt under nitrogenatmosfære. Så fore-tas inndamping til tørr tilstand, oppta-gelse i et egnet organisk oppløsningsmid-del, f. eks. alkohol eller alkohol/kloroform-blanding, avfiltrering fra uoppløst stoff og så er det som regel mulig å bringe diben-zylfosforsyreesteren av 4-hydroksy-indol-derivatet til krystallisering direkte. Hvor dette ikke lykkes, er det å anbefale en filtrering gjennom en søyle av aluminiumoksyd. The method can, for example, be carried out in the following way: For example, a 4-hydroxy-indole derivative of formula II in the form of the alkali salt is reacted with 1 mol of dibenzylphosphoryl chloride and 1 inert solvent, e.g. toluene, dimethoxyethane, tert. amyl alcohol etc., after which the solution is shaken or allowed to stand for a few hours at room temperature, possibly under a nitrogen atmosphere. Evaporation to a dry state is then carried out, absorption in a suitable organic solvent, e.g. alcohol or alcohol/chloroform mixture, filtering off undissolved matter and then it is usually possible to bring the dibenzyl phosphoric acid ester of the 4-hydroxy-indole derivative to crystallization directly. Where this is not successful, it is recommended to filter through a column of aluminum oxide.
Av den dibenzyl-fosforsyreester av 4-hydroksy-indol-derivatet som oppnås på denne måten blir benzylgruppene spaltet fra ved rysting i metanolisk oppløsning med en palladium-katalysator og hydro-gen, hvoretter den fosforsyreester som dan-nes, etter utskilling av katalysatoren, brin-ges til å krystallisere fra et passende opp-løsningsmiddel, fortrinnsvis metanol. Of the dibenzyl phosphoric acid ester of the 4-hydroxy-indole derivative obtained in this way, the benzyl groups are cleaved off by shaking in methanolic solution with a palladium catalyst and hydrogen, after which the phosphoric acid ester that is formed, after separation of the catalyst, is brought to crystallize from a suitable solvent, preferably methanol.
Det skal nå gis noen eksempler på hvorledes fremgangsmåten i henhold til oppfinnelsen kan gjennomføres. Alle tem-peraturer er angitt i °C. Smeltepunktene er ikke korrigert. Some examples will now be given of how the method according to the invention can be carried out. All temperatures are indicated in °C. The melting points are not corrected.
Eksempel 1. Example 1.
4- hydroksy- dimetyltryptamin-f osf orsyreester. 4-hydroxy-dimethyltryptamine phosphoric acid ester.
408 mg 4-hydroksy-dimetyltryptamin (2 millimol) ble overført til natriumsaltet med den beregnete mengde natrium-me-tylat i metanol. Inndampingsresten ble oppløst i 15'cms 1,2-dimetoksy-etan og rystet under nitrogenatmosfære i en time med 2 millimol dibenzyl-fosforylklorid. Så ble 408 mg of 4-hydroxydimethyltryptamine (2 millimoles) was transferred to the sodium salt with the calculated amount of sodium methylate in methanol. The evaporation residue was dissolved in 15 cms of 1,2-dimethoxyethane and shaken under a nitrogen atmosphere for one hour with 2 millimoles of dibenzyl phosphoryl chloride. Then
det igjen foretatt inndamping til tørr tilstand, resten ble opptatt i abs. kloroform, så ble det foretatt avfiltrering fra ikke opp-løst stoff og kloroformoppløsningen kromatografert på en søyle av aluminiumoksyd. Dibenzyl-fosforsyreesteren av 4-hydroksy-dimetyltryptamin ble vasket med kloroform + 5—10 pst. alkohol til filtratet. Den dannet et hvitt skum og kunne senere ikke krystalliseres. evaporation was again carried out to a dry state, the remainder was taken up in abs. chloroform, then filtration was carried out from undissolved matter and the chloroform solution chromatographed on a column of aluminum oxide. The dibenzyl phosphoric acid ester of 4-hydroxy-dimethyltryptamine was washed with chloroform + 5-10 per cent alcohol to the filtrate. It formed a white foam and later could not be crystallized.
350 mg 4-hydroksy-dimetyltryptamin-dibenzyl-fosforsyreester ble hydrert i 8 ems metanol i nærvær av en palladium-katalysator. Etter at hydrogenopptagelsen var stanset, ble det foretatt filtrering fra katalysatoren og filtratet forsiktig inndampet. 4-hydroksy-dimetyl-tryptaminfos-forsyreesteren krystalliserte under inn-damp ingen i små, f arveløse prismer. Smp. 210—212° (sp). Kellerfarvereaksjon: blå. 350 mg of 4-hydroxy-dimethyltryptamine-dibenzyl-phosphoric acid ester was hydrated in 8 ems methanol in the presence of a palladium catalyst. After the hydrogen absorption had stopped, filtration was carried out from the catalyst and the filtrate carefully evaporated. The 4-hydroxy-dimethyl-tryptamine-phosphoric acid ester crystallized under evaporation in small, colorless prisms. Temp. 210—212° (sp). Keller color reaction: blue.
Eksempel 2. Example 2.
4- hydroksy- dietyltryptamin-fosforsyreester. 4- hydroxydiethyltryptamine phosphoric acid ester.
1,19 g 4-hydroksy-dietyltryptamin ble overført til natriumsaltet med den beregnete mengde metanolisk natronlut under nitrogen og tørket i høy vakuum ved 60°. Så ble det foretatt oppløsning i 20 cm3 dimetoksyetan, blanding med en oppløs-ning av 1,53 g dibenzyl-fosforylklorid i tetraklorkullstoff og rysting i 18 timer ved romtemperatur. Det ble så foretatt klar-filtrering, filtratet ble inndampet til tørr tilstand og resten kromatografert på 60 g aluminiumoksyd. 4-hydroksy-dietyltryptamin-dibenzyl-fosforsyreester ble vasket med kloroform + 10—20 pst. alkohol til filtrat. Det kunne ikke krystalliseres fra noe oppløsningsmiddel. 1,4 g 4-hydroksy-dietyltryptamin-dibenzyl-fosforsyreester ble hydrert i 50 ems metanol i nærvær av en palladiumkatalysator. Etter at hydrogenopptagelsen var stanset, ble det foretatt filtrering, katalysatoren ble vasket med varm metanol og de forente metanol-oppløsninger inndampet. 4-hydroksy-dietyltryptamin-fosforsyreester krystalliserte herunder i prismer med sirip. 257°. Kellerfarvereaksjon: blå-violett. 1.19 g of 4-hydroxy-diethyltryptamine was transferred to the sodium salt with the calculated amount of methanolic caustic soda under nitrogen and dried in high vacuum at 60°. Dissolution was then carried out in 20 cm 3 of dimethoxyethane, mixing with a solution of 1.53 g of dibenzyl phosphoryl chloride in carbon tetrachloride and shaking for 18 hours at room temperature. Clear filtration was then carried out, the filtrate was evaporated to dryness and the residue chromatographed on 60 g of aluminum oxide. 4-Hydroxy-diethyltryptamine-dibenzyl-phosphoric acid ester was washed with chloroform + 10-20% alcohol to filtrate. It could not be crystallized from any solvent. 1.4 g of 4-hydroxy-diethyltryptamine-dibenzyl-phosphoric acid ester was hydrated in 50 ems methanol in the presence of a palladium catalyst. After the hydrogen absorption had stopped, filtration was carried out, the catalyst was washed with hot methanol and the combined methanol solutions were evaporated. 4-Hydroxy-diethyltryptamine phosphoric acid ester crystallized below in syrupy prisms. 257°. Keller color reaction: blue-violet.
Eksempel 3. Example 3.
4- hydroksy- 3-( 2'- piperidino- etyl) - 4- hydroxy- 3-( 2'- piperidino- ethyl) -
indol- f osf orsyreester. indole phosphoric acid ester.
1,35 g 4-hydroksy-3-(2'-piperidino-etyl)-indol ble oppløst i 30 cm» metanol, 1.35 g of 4-hydroxy-3-(2'-piperidino-ethyl)-indole was dissolved in 30 cm» of methanol,
blandet med 5,64 ems 0,96-n. NaOH og mixed with 5.64 ems 0.96-n. NaOH and
inndampet under nitrogen til tørr tilstand. evaporated under nitrogen to dryness.
Resten ble opptatt i 30 ems dimetoksy-etan, en oppløsning av dibenzyl-fosforylklorid i 20 cm» tetraklorkullstoff, som var The residue was taken up in 30 ems of dimethoxyethane, a solution of dibenzyl phosphoryl chloride in 20 cm" of carbon tetrachloride, which was
fremstillet av 1,45 g dibenzylfosfitt, ble til-satt og blandingen rystet i 20 timer. Det prepared from 1.45 g of dibenzyl phosphite, was added and the mixture shaken for 20 hours. The
utskilte koksalt ble så filtrert fra, filtratet secreted sodium chloride was then filtered from, the filtrate
inndampet og resten kromatografert på evaporated and the residue chromatographed on
den 30-dobbelte mengde aluminiumoksyd. the 30-fold amount of aluminum oxide.
4-hydroksy-3- (2'-piperidino-etyl) -indol-dibenzyl-fosforsyreesteren ble vasket med The 4-hydroxy-3-(2'-piperidino-ethyl)-indole-dibenzyl phosphoric acid ester was washed with
kloroform til tiltrat. Amorft skum som chloroform to titrate. Amorphous foam like
ikke kunne krystalliseres fra noe oppløs-ningsmiddel. could not be crystallized from any solvent.
En oppløsning av 2 g 4-hydroksy-3-(2'-piperidino-etyl)-indol-dibenzyl-fosforsyreester i 20 cm3 metanol ble rystet med 1 g palladium-katalysator og hydro-gen inntil hydrogenopptagelsen stanset. Derpå ble det foretatt filtrering, nedsla-get ble kokt med vann og de forente filt-rater ble inndampet til lite volum. Der-under krystalliserte 4-hydroksy-3-(2'-piperidino-etyl)-indol-fosforsyreesteren ut i A solution of 2 g of 4-hydroxy-3-(2'-piperidino-ethyl)-indole-dibenzyl-phosphoric acid ester in 20 cm 3 of methanol was shaken with 1 g of palladium catalyst and hydrogen until the hydrogen absorption stopped. Filtration was then carried out, the residue was boiled with water and the combined filtrates were evaporated to a small volume. There-under, the 4-hydroxy-3-(2'-piperidino-ethyl)-indole phosphoric acid ester crystallized out in
form av farveløse prismer med smp. 260— form of colorless prisms with m.p. 260—
262°. Kellerfarvereaksjon: violett. Van 262°. Keller color reaction: violet. Used to
Urk-farvereaksjon: brun-orange. Urk color reaction: brown-orange.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1226769A CH502940A (en) | 1967-06-07 | 1969-08-11 | Hay conveyor and distribution system with fan |
Publications (2)
Publication Number | Publication Date |
---|---|
NO133068B true NO133068B (en) | 1975-11-24 |
NO133068C NO133068C (en) | 1976-03-03 |
Family
ID=4381425
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO305370A NO133068C (en) | 1969-08-11 | 1970-08-10 |
Country Status (11)
Country | Link |
---|---|
AT (1) | AT306632B (en) |
BE (1) | BE754480A (en) |
CH (1) | CH505743A (en) |
DE (2) | DE1943334B2 (en) |
DK (1) | DK140081B (en) |
ES (1) | ES382503A1 (en) |
FR (1) | FR2057910A5 (en) |
GB (1) | GB1279164A (en) |
NL (1) | NL7011866A (en) |
NO (1) | NO133068C (en) |
SE (1) | SE354835B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3114137A1 (en) * | 1981-04-08 | 1982-11-04 | Johannes Stieve GmbH, 4520 Melle | Conveying device, in particular for agricultural harvested crops |
CN107810723B (en) * | 2017-11-20 | 2020-09-15 | 安徽德鑫源食品有限公司 | Intelligent control constant-pressure grain storage equipment |
-
1969
- 1969-08-11 CH CH1187670A patent/CH505743A/en not_active IP Right Cessation
- 1969-08-25 AT AT810869A patent/AT306632B/en not_active IP Right Cessation
- 1969-08-26 DE DE19691943334 patent/DE1943334B2/en not_active Ceased
- 1969-08-26 DE DE19696933544 patent/DE6933544U/en not_active Expired
-
1970
- 1970-07-31 FR FR7028438A patent/FR2057910A5/fr not_active Expired
- 1970-08-04 SE SE1065570A patent/SE354835B/xx unknown
- 1970-08-06 ES ES382503A patent/ES382503A1/en not_active Expired
- 1970-08-06 BE BE754480D patent/BE754480A/en unknown
- 1970-08-07 GB GB3819470A patent/GB1279164A/en not_active Expired
- 1970-08-10 DK DK408870A patent/DK140081B/en unknown
- 1970-08-10 NO NO305370A patent/NO133068C/no unknown
- 1970-08-11 NL NL7011866A patent/NL7011866A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DE6933544U (en) | 1970-12-10 |
DK140081C (en) | 1979-11-19 |
FR2057910A5 (en) | 1971-05-21 |
DE1943334A1 (en) | 1971-02-25 |
NO133068C (en) | 1976-03-03 |
DK140081B (en) | 1979-06-18 |
ES382503A1 (en) | 1972-12-01 |
AT306632B (en) | 1973-04-25 |
CH505743A (en) | 1971-04-15 |
BE754480A (en) | 1971-01-18 |
SE354835B (en) | 1973-03-26 |
DE1943334B2 (en) | 1974-07-25 |
GB1279164A (en) | 1972-06-28 |
NL7011866A (en) | 1971-02-15 |
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