CH467744A - Process for the preparation of 5H-dibenzo- (a, d) -cycloheptenes - Google Patents
Process for the preparation of 5H-dibenzo- (a, d) -cycloheptenesInfo
- Publication number
- CH467744A CH467744A CH1531868A CH1531868A CH467744A CH 467744 A CH467744 A CH 467744A CH 1531868 A CH1531868 A CH 1531868A CH 1531868 A CH1531868 A CH 1531868A CH 467744 A CH467744 A CH 467744A
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- carbon atoms
- formula
- alkyl
- dibenzo
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/31—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by at least three rings
- C07C211/32—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by at least three rings containing dibenzocycloheptane or dibenzocycloheptene ring systems or condensed derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
- C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Display Racks (AREA)
Description
Verfahren zur Herstellung von 5H-Dibenzo-(1, d)-cycloheptenen
IDie vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung von neuen 5H-Dibenzo-(a,d)- cycloheptenen und deren Salze, welche am Kohlenstoff atom der 5-Stellung durch einen Aminopropylidenrest substituiert sind.
Diese Verbindungen können zur Behandlung von Geisteskrankheiten verwendet werden, da sie als Mittel gegen Depressionszustände bzw. zur Aufheiterung des Gemüts und als psychische Energiespender wirksam sind. Für solche Fälle kann die tägliche Dosis 5 bis 250 mlg betragen, welche vorzugsweise in Teildosen eingenommen wird. Diese Verbindungen werden vorzugsweise in Form ihrer mit Säuren erhältlichen Salze verabreicht.
Die nach dem erfindugnsgemässen Verfahren herstellbaren Verbindungen haben folgende Formel:
EMI1.1
worin X und X' Wasserstoff; eine Alkylgruppe oder eine Alkenylgruppe mit bis zu 6 Kohlenstoffatomen; eine Perfluoralkylgruppe mit bis zu 4 Kohlenstoffatomen; ein Phenyl- oder substituiertes Phenylradikal, leine Acylgruppe oder eine Perfluoracylgruppe mit bis zu 4 Kohlenstoffatomen; eine Aminogruppe, eine Alkylaminogruppe mit bis zu 4 Kohlenstoffatomen; eine Dialkyl laminogruppe mit bis zu 6 Kohlenstoffatomen ; eine Acyi- aminogruppe oder eine Perfluoracylaminogruppe oder eine Alkylsulfonylaminogruppe mit bis zu 4 Kohlenstoffatomen ; Halogen;
Hydroxyl; eine Alkoxygruppe oder leine Perfluor. alkoxygruppe, mit Es zu 4 Kohlenstoffatomen; Cyan; Carboxy; Carbamyl; eine alkylcarbamylgruppe mit bis zu 5 Kohlenstoffatomen; eine Dialkyl- carbamylgruppe mit Ibis zu 9 Kohlenstoffatomen; eine Carbalkoxygruppe mit bis zu 6 Kohlenstoffatomen; Mercapto- oder eine Alkylmercaptogruppe oder eine Alkylsulfonylgruppe oder eine Perfluoralkylsulfonylgruppe mit bis zu 4 Kohlenstoffatomen;
Sulfamyl; eine Alkyl lsulfamylgruppe mit bis zu 4 Kohlenstoffatomen oder eine Dialkylsulfamylgruppe mit bis zu 6 Kohlenstoff atomen und R und R' Wasserstoff; eine Alkyl-, Alkenyl-, Alkoxy- oder Cycloalkylgruppe mit je bis zu 6 Kohlenstoffatomen; Phenyl; substituiertes Phenyl oder Aralkyl, z. B. Benzyl, bedeuten.
Das erfindungsgemässe Verfahren betrifft nun die Umwandlung eines entsprechenden primären Amins in das sekundäre Amin der genannten Formel, und ist da durch gekennzeichnet, dass man ein primäres Amil der Formel
EMI1.2
mit einem Keton oder einem Aldehyd in einem Lösungsmittel bei Rückflusstempertur unter Bildung einer Verbindung der Formel
EMI1.3
zur Reaktion bringt und Idiese Verbindung in Gegenwart eines Palladium-Katalysators zum sekundären Amin der Formel
EMI2.1
hydriert.
Das erhaltene Produkt kann man leicht in die entsprechenden Salze überführen.
Die Umsetzung mit dem Keton oder Aldehyd erfolgt vorzugsweise in Benzol oder Toluol als Lösungsmittel unter Erhitzen des Gemisches zum Rückfluss, worauf die Hydrierung in Gegenwart eines Palladium-Katalysa- tors erfolgt.
Dieses Verfahren zur Überführung Ides primären in das sekundäre Amin ist insbesondere dann von Vorteil, wenn grössere Gruppen eingeführt werden als Methylgruppen.
Die Herstellung des Ausgangsstoffes ist im schweizerischen Patent Nr. 464 893 beschrieben.
Beispiel 1 S-(3-Butylaminopropyliden)-5H-dibenzo- (a,d)-cyclohepten
Einer Lösung von 5-(3-aminopropyliden)-5H-dibenzo-(a,d)-cyclohepten in Benzol wird Butyraldehyd zugefügt und man erhitzt die Mischung zum Rückfluss unter Kontinuierlicher Wasserabscheidung, bis letztere beendet ist. nach Abdampfen des Benzols wird das gebildete 5-(3-Butylidenaminopropyliden)-5H-dibenzo-(a,d) cyclohepten unter vermindertem Druck destilliert, in absolutem Alkohol gelost und in Gegenwart eines Platinkatalysdators hydriert. Nach Abfiltrieren vom Katalysator und Wegdestillieren des Lösungsmittel wird das Produkt durch Destillation unter reduziertem Druck gereinigt.
Beispiel 2
Man hydriert eine Lösung von 5-(3-Aminopropyliden)-5H-dibenzo-(a,d)-cyclohepten und von diesem gegenüber überschüssigem Aceton in Äthanol und trennt gemäss Verfahren nach Beispiel 1. Das erhaltene Produkt ist 5-(3-Isopropylaminopropyliden)-5H-dibenzo (a,d)-cyclohepten.
Process for the preparation of 5H-dibenzo- (1, d) -cycloheptenes
The present invention relates to a process for the preparation of new 5H-dibenzo- (a, d) - cycloheptenes and their salts, which are substituted on the carbon atom of the 5-position by an aminopropylidene radical.
These compounds can be used to treat mental illnesses because they are effective as an antidepressant agent or to cheer up the mind and as a psychic energizer. In such cases, the daily dose can be 5 to 250 mlg, which is preferably taken in divided doses. These compounds are preferably administered in the form of their salts obtainable with acids.
The compounds which can be prepared by the process according to the invention have the following formula:
EMI1.1
wherein X and X 'are hydrogen; an alkyl group or an alkenyl group of up to 6 carbon atoms; a perfluoroalkyl group of up to 4 carbon atoms; a phenyl or substituted phenyl radical, an acyl group or a perfluoroacyl group of up to 4 carbon atoms; an amino group, an alkylamino group of up to 4 carbon atoms; a dialkylamino group of up to 6 carbon atoms; an acylamino group or a perfluoroacylamino group or an alkylsulfonylamino group with up to 4 carbon atoms; Halogen;
Hydroxyl; an alkoxy group or a nonperfluoro group. alkoxy group, with Es to 4 carbon atoms; Cyan; Carboxy; Carbamyl; an alkylcarbamyl group of up to 5 carbon atoms; a dialkylcarbamyl group with ibis of 9 carbon atoms; a carbalkoxy group of up to 6 carbon atoms; Mercapto or an alkyl mercapto group or an alkylsulfonyl group or a perfluoroalkylsulfonyl group with up to 4 carbon atoms;
Sulfamyl; an alkyl isulfamyl group with up to 4 carbon atoms or a dialkylsulfamyl group with up to 6 carbon atoms and R and R 'are hydrogen; an alkyl, alkenyl, alkoxy or cycloalkyl group each having up to 6 carbon atoms; Phenyl; substituted phenyl or aralkyl, e.g. B. benzyl.
The process according to the invention now relates to the conversion of a corresponding primary amine into the secondary amine of the formula mentioned, and is characterized in that a primary amil of the formula
EMI1.2
with a ketone or an aldehyde in a solvent at reflux temperature to form a compound of the formula
EMI1.3
brings this compound to reaction in the presence of a palladium catalyst to the secondary amine of the formula
EMI2.1
hydrogenated.
The product obtained can easily be converted into the corresponding salts.
The reaction with the ketone or aldehyde is preferably carried out in benzene or toluene as the solvent, with the mixture being heated to reflux, whereupon the hydrogenation takes place in the presence of a palladium catalyst.
This process for converting the primary into the secondary amine is particularly advantageous when larger groups than methyl groups are introduced.
The production of the starting material is described in Swiss Patent No. 464 893.
Example 1 S- (3-butylaminopropylidene) -5H-dibenzo- (a, d) -cycloheptene
Butyraldehyde is added to a solution of 5- (3-aminopropylidene) -5H-dibenzo- (a, d) -cycloheptene in benzene and the mixture is heated to reflux with continuous separation of water until the latter has ended. After the benzene has evaporated, the 5- (3-butylideneaminopropylidene) -5H-dibenzo- (a, d) cycloheptene formed is distilled under reduced pressure, dissolved in absolute alcohol and hydrogenated in the presence of a platinum catalyst. After the catalyst has been filtered off and the solvent has been distilled off, the product is purified by distillation under reduced pressure.
Example 2
A solution of 5- (3-aminopropylidene) -5H-dibenzo- (a, d) -cycloheptene and excess acetone from this in ethanol is hydrogenated and separated according to the method of Example 1. The product obtained is 5- (3-isopropylaminopropylidene ) -5H-dibenzo (a, d) -cycloheptene.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12083561A | 1961-05-24 | 1961-05-24 | |
US14022361A | 1961-09-25 | 1961-09-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH467744A true CH467744A (en) | 1969-01-31 |
Family
ID=26818813
Family Applications (7)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1532268A CH467743A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of dibenzocycloheptenes |
CH1531868A CH467744A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of 5H-dibenzo- (a, d) -cycloheptenes |
CH1104067A CH464900A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of dibenzocycloheptenes |
CH628562A CH464893A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of dibenzocycloheptenes |
CH1532168A CH465599A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of dibenzocycloheptenes |
CH1531968A CH467238A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of 5H-dibenzo- (a, d) -cycloheptenes |
CH1532068A CH464903A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of dibenzocycloheptenes |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1532268A CH467743A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of dibenzocycloheptenes |
Family Applications After (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1104067A CH464900A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of dibenzocycloheptenes |
CH628562A CH464893A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of dibenzocycloheptenes |
CH1532168A CH465599A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of dibenzocycloheptenes |
CH1531968A CH467238A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of 5H-dibenzo- (a, d) -cycloheptenes |
CH1532068A CH464903A (en) | 1961-05-24 | 1962-05-24 | Process for the preparation of dibenzocycloheptenes |
Country Status (13)
Country | Link |
---|---|
BE (1) | BE617967A (en) |
BR (1) | BR6239240D0 (en) |
CH (7) | CH467743A (en) |
CY (1) | CY354A (en) |
DE (2) | DE1468212A1 (en) |
DK (6) | DK110035C (en) |
FI (3) | FI41391B (en) |
FR (1) | FR2516M (en) |
GB (1) | GB1008263A (en) |
GT (1) | GT197016875A (en) |
MY (1) | MY6700003A (en) |
NO (1) | NO121833B (en) |
SE (8) | SE317369B (en) |
-
1962
- 1962-05-16 GB GB18913/62A patent/GB1008263A/en not_active Expired
- 1962-05-18 FI FI1007/62A patent/FI41391B/fi active
- 1962-05-21 DE DE19621468212 patent/DE1468212A1/en active Pending
- 1962-05-21 DE DE19621593098 patent/DE1593098A1/en active Pending
- 1962-05-22 BE BE617967A patent/BE617967A/en unknown
- 1962-05-22 BR BR139240/62A patent/BR6239240D0/en unknown
- 1962-05-23 DK DK232162AA patent/DK110035C/en active
- 1962-05-23 DK DK166663AA patent/DK106326C/en active
- 1962-05-23 DK DK106064AA patent/DK108151C/en active
- 1962-05-23 DK DK106264AA patent/DK106278C/en active
- 1962-05-23 DK DK106164AA patent/DK107420C/en active
- 1962-05-23 NO NO144482A patent/NO121833B/no unknown
- 1962-05-24 CH CH1532268A patent/CH467743A/en unknown
- 1962-05-24 CH CH1531868A patent/CH467744A/en unknown
- 1962-05-24 CH CH1104067A patent/CH464900A/en unknown
- 1962-05-24 CH CH628562A patent/CH464893A/en unknown
- 1962-05-24 CH CH1532168A patent/CH465599A/en unknown
- 1962-05-24 SE SE5885/62A patent/SE317369B/xx unknown
- 1962-05-24 SE SE13207/65A patent/SE325269B/xx unknown
- 1962-05-24 CH CH1531968A patent/CH467238A/en unknown
- 1962-05-24 CH CH1532068A patent/CH464903A/en unknown
- 1962-08-22 FR FR907533A patent/FR2516M/en active Active
-
1964
- 1964-02-27 DK DK97064AA patent/DK111679B/en unknown
-
1965
- 1965-05-14 SE SE635365A patent/SE318869B/xx unknown
- 1965-10-12 SE SE13209/65A patent/SE326441B/xx unknown
- 1965-10-12 SE SE13204/65A patent/SE323364B/xx unknown
- 1965-10-12 SE SE13205/65A patent/SE326440B/xx unknown
- 1965-10-12 SE SE13210/65A patent/SE325874B/xx unknown
- 1965-10-12 SE SE13211/65A patent/SE326442B/xx unknown
-
1966
- 1966-10-03 FI FI2588/66A patent/FI41647B/fi active
- 1966-10-03 FI FI2587/66A patent/FI41646B/fi active
- 1966-10-14 CY CY35466A patent/CY354A/en unknown
-
1967
- 1967-12-31 MY MY19673A patent/MY6700003A/en unknown
-
1970
- 1970-05-11 GT GT197016875A patent/GT197016875A/en unknown
Also Published As
Publication number | Publication date |
---|---|
SE323364B (en) | 1970-05-04 |
DK108151C (en) | 1967-09-25 |
GT197016875A (en) | 1971-11-02 |
DK111679B (en) | 1968-09-30 |
SE326442B (en) | 1970-07-27 |
DE1468212A1 (en) | 1969-01-02 |
FR2516M (en) | 1964-05-11 |
CY354A (en) | 1966-10-14 |
SE326441B (en) | 1970-07-27 |
DK107420C (en) | 1967-05-29 |
DK106278C (en) | 1967-01-16 |
DK106326C (en) | 1967-01-23 |
CH464893A (en) | 1968-11-15 |
SE318869B (en) | 1969-12-22 |
BE617967A (en) | 1962-11-22 |
FI41647B (en) | 1969-09-30 |
DK110035C (en) | 1968-09-02 |
DE1593098A1 (en) | 1969-10-16 |
FI41646B (en) | 1969-09-30 |
MY6700003A (en) | 1967-12-31 |
BR6239240D0 (en) | 1973-05-24 |
CH467743A (en) | 1969-01-31 |
CH465599A (en) | 1968-11-30 |
CH467238A (en) | 1969-01-15 |
SE325874B (en) | 1970-07-13 |
FI41391B (en) | 1969-07-31 |
NO121833B (en) | 1971-04-19 |
SE326440B (en) | 1970-07-27 |
CH464900A (en) | 1968-11-15 |
CH464903A (en) | 1968-11-15 |
SE325269B (en) | 1970-06-29 |
GB1008263A (en) | 1965-10-27 |
SE317369B (en) | 1969-11-17 |
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