CH434283A - Process for the preparation of substituted alkylamines - Google Patents
Process for the preparation of substituted alkylaminesInfo
- Publication number
- CH434283A CH434283A CH1439465A CH1439465A CH434283A CH 434283 A CH434283 A CH 434283A CH 1439465 A CH1439465 A CH 1439465A CH 1439465 A CH1439465 A CH 1439465A CH 434283 A CH434283 A CH 434283A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- formula
- halogen
- lower alkyl
- parts
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/12—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by hydroxy groups
-
- 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
- C07C211/27—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 having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung von substituierten Aklkylaminen
Durch die belgische Patentschrift 588 736 sind Verbindungen der allgemeinen Formel:
EMI1.1
bekannt geworden. In dieser Formel bedeutet R' Wasserstoff, eine Hydroxylgruppe, ein Halogen oder eine niedere Alkylgruppe. R" ist Wasserstoff oder eine Methylgruppe. Alk bedeutet eine niedere Alkylgruppe mit 2 oder 3 C-Atomen, und X ist eine Hydroxylgruppe oder Chlor oder Brom. Diese Verbindungen haben eine zentralstimulierende Wirkung.
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Verbindungen der Formel:
EMI1.2
In dieser Formel bedeutet R' Wasserstoff, eine Hydroxylgruppe, ein Halogen oder eine niedere Alkylgruppe. R" und R"' sind niedere Alkylgruppen mit 1 bis 3 C-Atomen, die auch zu einem fünf- bis sechsgliedrigen Ring geschlossen sein können. Alk ist eine niedere gerade oder verzweigte Alkylengruppe mit 2 oder 3 C-Atomen und Hal ein Halogenatom. Das Verfahren ist dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.3
mit einer Verbindung umsetzt, die fähig ist, eine aliphatische Hydroxylgruppe durch Halogen zu ersetzen.
Verbindungen der vorstehenden Formel II können bei spielsweise erhalten werden nach dem Verfahren des
Patentes Nr. 403 797.
Als Halogenierungsmittel für das erfindungsgemässe
Verfahren eignen sich z. B. Halogenwasserstoffsäuren in Gegenwart oder Abwesenheit von Katalysatoren (z. B. Zinkchlorid, konz. Schwefelsäure) anorganische
Polyhalogenide, wie Phosphorpentachlorid, Phosphor trichlorid, Thionylchlorid, Phosgen, Phosphoroxy chlorid, Sulfurylchlorid und dgl.
Die nach der Erfindung hergestellten neuen Ver bindungen wirken zentralstimulierend und appetit zügelnd.
Beispiel 1
15 Teile 1-(p-Chlorphenyl)-2-methyl-2-oxyäthyl- amino-propan werden in 100 Teilen Chloroform gelöst, die Lösung mit Salzsäure gesättigt und zum Rückfluss erhizt. Dann lässt man 12 Teile Zinnchlorid zutropfen und kocht eine Stunde lang. Anschliessend wird zur
Trockene eingedampft und der Rückstand aus Isoprop anol mit Kohle umkristallisiert. Man erhält 12 Teile l-(p-Chlorphenyl)-2-methyl-chloräthylamino-propan als
Hydrochlorid. Der Schmelzpunkt liegt bei 179-1800 C.
Beispiel 2
Setzt man 16 Teile l-Phenyl-2-methyl-2-oxyäthyl- amino-propan in 100 Teilen Chloroform mit gasförmiger Salzsäure und mit 15 Teilen Thionylchlorid in gleicher Weise um, wie in Beispiel 1 beschrieben, so erhält man 12 Teile 1 -Phenyl-2-methyl-2-chloräthylaminopropan-Hydrochlorid mit dem Schmelzpunkt 180 181" C.
Beispiel 3
Bei Verwendung von 1-(p-Methoxyphenyl)-2-meth yl-2-oxyäthylamino-propan und gleicher Verfahrensweise wie in Beispiel 1 wird 1-(p-Methoxyphenyl)-2 methyl-2-chloräthyl-amino-propan-Hydrochlorid mit dem Schmelzpunkt 198-199 C erhalten.
Beispiel 4
Bei Verwendung von 1-Benzyl-l-oxyäthylamino- cyclohexan wird analog zu Beispiel 1 l-Benzyl-l-chlor- äthyl-amino-cyclohexan vom Schmelzpunkt 205-2060 C erhalten.
Process for the preparation of substituted alkylamines
The Belgian patent specification 588 736 gives compounds of the general formula:
EMI1.1
known. In this formula, R 'denotes hydrogen, a hydroxyl group, a halogen or a lower alkyl group. R "is hydrogen or a methyl group. Alk means a lower alkyl group with 2 or 3 carbon atoms, and X is a hydroxyl group or chlorine or bromine. These compounds have a central stimulating effect.
The present invention relates to a process for the preparation of compounds of the formula:
EMI1.2
In this formula, R 'denotes hydrogen, a hydroxyl group, a halogen or a lower alkyl group. R "and R" 'are lower alkyl groups with 1 to 3 carbon atoms, which can also be closed to form a five- to six-membered ring. Alk is a lower straight or branched alkylene group with 2 or 3 C atoms and Hal is a halogen atom. The process is characterized in that a compound of the formula
EMI1.3
with a compound capable of replacing an aliphatic hydroxyl group with halogen.
Compounds of the above formula II can be obtained, for example, by the process of
Patent No. 403,797.
As a halogenating agent for the inventive
Methods are suitable e.g. B. hydrohalic acids in the presence or absence of catalysts (z. B. zinc chloride, conc. Sulfuric acid) inorganic
Polyhalides such as phosphorus pentachloride, phosphorus trichloride, thionyl chloride, phosgene, phosphorus oxy chloride, sulfuryl chloride and the like.
The new compounds produced according to the invention have a central stimulating effect and suppress the appetite.
example 1
15 parts of 1- (p-chlorophenyl) -2-methyl-2-oxyethylamino-propane are dissolved in 100 parts of chloroform, the solution is saturated with hydrochloric acid and heated to reflux. Then 12 parts of tin chloride are added dropwise and the mixture is boiled for one hour. Then the
Evaporated dry and the residue from isopropanol with charcoal recrystallized. 12 parts of 1- (p-chlorophenyl) -2-methyl-chloroethylamino-propane are obtained as
Hydrochloride. The melting point is 179-1800 C.
Example 2
If 16 parts of 1-phenyl-2-methyl-2-oxyethylamino-propane are reacted in 100 parts of chloroform with gaseous hydrochloric acid and with 15 parts of thionyl chloride in the same way as described in Example 1, 12 parts of 1-phenyl are obtained -2-methyl-2-chloroethylaminopropane hydrochloride with a melting point of 180 181 "C.
Example 3
When using 1- (p-methoxyphenyl) -2-meth yl-2-oxyethylaminopropane and the same procedure as in Example 1, 1- (p-methoxyphenyl) -2 methyl-2-chloroethylamino-propane hydrochloride is used the melting point 198-199 ° C obtained.
Example 4
When using 1-benzyl-1-oxyethylamino-cyclohexane, analogously to Example 1, 1-benzyl-1-chloroethylamino-cyclohexane with a melting point of 205-2060 ° C. is obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED35763A DE1244197B (en) | 1961-03-29 | 1961-03-29 | Process for the preparation of substituted beta-phenylaethylamines and their acid addition salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH434283A true CH434283A (en) | 1967-04-30 |
Family
ID=7042790
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209862A CH403797A (en) | 1961-03-29 | 1962-02-21 | Process for the preparation of substituted alkylamines |
| CH1439465A CH434283A (en) | 1961-03-29 | 1962-02-21 | Process for the preparation of substituted alkylamines |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209862A CH403797A (en) | 1961-03-29 | 1962-02-21 | Process for the preparation of substituted alkylamines |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE615731A (en) |
| CH (2) | CH403797A (en) |
| DE (1) | DE1244197B (en) |
| FI (1) | FI40544B (en) |
| GB (1) | GB959958A (en) |
| SE (1) | SE308528B (en) |
-
1961
- 1961-03-29 DE DED35763A patent/DE1244197B/en active Pending
-
1962
- 1962-02-21 CH CH209862A patent/CH403797A/en unknown
- 1962-02-21 CH CH1439465A patent/CH434283A/en unknown
- 1962-02-26 FI FI0401/62A patent/FI40544B/fi active
- 1962-03-14 GB GB9807/62A patent/GB959958A/en not_active Expired
- 1962-03-28 BE BE615731A patent/BE615731A/en unknown
- 1962-03-28 SE SE3466/62A patent/SE308528B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB959958A (en) | 1964-06-03 |
| FI40544B (en) | 1968-11-30 |
| DE1244197B (en) | 1967-07-13 |
| BE615731A (en) | 1962-07-16 |
| CH403797A (en) | 1965-12-15 |
| SE308528B (en) | 1969-02-17 |
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