DE874909C - Process for the preparation of saturated derivatives of ethylamine - Google Patents
Process for the preparation of saturated derivatives of ethylamineInfo
- Publication number
- DE874909C DE874909C DEK2793D DEK0002793D DE874909C DE 874909 C DE874909 C DE 874909C DE K2793 D DEK2793 D DE K2793D DE K0002793 D DEK0002793 D DE K0002793D DE 874909 C DE874909 C DE 874909C
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- ethylamine
- hydrogen
- alkyl
- hepten
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000003947 ethylamines Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 229920006395 saturated elastomer Polymers 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
- -1 methylcyclohexyl Chemical group 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000002921 anti-spasmodic effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- DOAWJRLLPYCTHR-UHFFFAOYSA-N 3-methyloct-2-en-2-amine Chemical compound CCCCCC(C)=C(C)N DOAWJRLLPYCTHR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- IFYLVUHLOOCYBG-UHFFFAOYSA-N eticyclidine Chemical compound C=1C=CC=CC=1C1(NCC)CCCCC1 IFYLVUHLOOCYBG-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 102220095346 rs876658161 Human genes 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von gesättigten Derivaten des Äthylamins Es wurde gefunden, daB die gesättigten Derivate des Äthylamins der allgemeinen Formel worin R, ein Alkyl mit mindestens q. Kohlenstoffatomen in gerader oder verzweigter Kette, R2 Wasserstoff, Alkyl, Cycloalkyl oder Arylalkyl und R3 Alkyl oder Cycloalkyl mit höchstens 7 Kohlenstoffatomen bedeuten, günstige krampflösende Eigenschaften haben. Darüber hinaus zeichnen sich die neuen Verbindungen durch lokalanästhetischeWirkung aus und sind in bezug auf diese Wirkung und ihre Toxizität bekannten Lokalanästhetika überlegen.Process for the preparation of saturated derivatives of ethylamine It has been found that the saturated derivatives of ethylamine of the general formula wherein R, an alkyl of at least q. Carbon atoms in a straight or branched chain, R2 denotes hydrogen, alkyl, cycloalkyl or arylalkyl and R3 denotes alkyl or cycloalkyl with a maximum of 7 carbon atoms, have favorable antispasmodic properties. In addition, the new compounds are distinguished by a local anesthetic effect and with regard to this effect and their toxicity are superior to known local anesthetics.
R1 kann z. B. Butyl, Isobutyl, Amyl, Isoamyl, Hexyl, Heptyl oder einen anderen gesättigten Kohlenwasserstoffrest bedeuten. R2 bedeutet Wasserstoff, einen Alkylrest, z. B. Methyl, Äthyl, Propyl, Isopropyl, Butyl, Isobutyl, Amyl, Isoamyl usw., oder einen Cycloalkylrest, z. B. Cyclopentyl, Cyclohexyl, Methylcyclohexyl usw., oder einen Arylalkylrest, z. B. Phenylmethyl, Phenyläthyl, Phenylpropyl usw.R1 can e.g. B. butyl, isobutyl, amyl, isoamyl, hexyl, heptyl or one mean another saturated hydrocarbon radical. R2 means hydrogen, one Alkyl radical, e.g. B. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl etc., or a cycloalkyl radical, e.g. B. cyclopentyl, cyclohexyl, methylcyclohexyl etc., or an arylalkyl radical, e.g. B. Phenylmethyl, Phenyläthyl, Phenylpropyl etc.
R3 bedeutet ein Alkyl oder Cycloalkyl mit höchstens 7 Kohlenstoffatomen, beispielsweise der bei R2 angegebenen Art. Die neuen - Verbindungen werden in Abänderung des Verfahrens gemäß Patent 76719s dadurch hergestellt, daß man ungesättigte Abkömmlinge des Athylamins der allgemeinen Formel worin R1, R2 und R3 die oben angegebene Bedeutung haben und mindestens ein R eine Doppelbindung aufweist, so daß n mindestens gleich i ist, hydriert.R3 denotes an alkyl or cycloalkyl with a maximum of 7 carbon atoms, for example of the type indicated for R2. The new compounds are prepared in a modification of the process according to patent 76719s by using unsaturated derivatives of ethylamine of the general formula in which R1, R2 and R3 have the meaning given above and at least one R has a double bond, so that n is at least equal to i, hydrogenated.
In Ausübung der Erfindung kann man von ungesättigten Abkömmlingen des Äthylamins ausgehen, die eine Doppelbindung aufweisen und somit die allgemeine Formel haben. Hierbei kann die Doppelbindung entweder im R1 oder im R2 oder im R3 enthalten sein, entsprechend den folgenden Formeln worin R'1 ein Alkenyl mit mindestens 4 Kohlenstoffatomen in gerader oder verzweigter Kette, z. B. ein Butenyl, Pentenyl, Hexenyl, Heptenyl, Octenyl usw., R'2 Wasserstoff oder ein Alkenyl, z. B. Allyl, Butenyl, Pentenyl, oder ein Cycloalkenyl, z. B. Cyclopentenyl oder Cyclohexenyl, oder ein Arylalkenyl, z. B. PHenylallyl, und R'3 ein Alkenyl oder ein Cycloalkenyl mit höchstens 7 Kohlenstoffatomen der bei R'2 angegebenen Art bedeuten.When practicing the invention, one can start from unsaturated derivatives of ethylamine which have a double bond and thus the general formula to have. The double bond here can be contained either in R1 or in R2 or in R3, according to the following formulas wherein R'1 is an alkenyl having at least 4 carbon atoms in a straight or branched chain, e.g. B. a butenyl, pentenyl, hexenyl, heptenyl, octenyl etc., R'2 is hydrogen or an alkenyl, e.g. B. allyl, butenyl, pentenyl, or a cycloalkenyl, e.g. B. cyclopentenyl or cyclohexenyl, or an arylalkenyl, e.g. B. PHenylallyl, and R'3 is an alkenyl or a cycloalkenyl with a maximum of 7 carbon atoms of the type indicated for R'2.
So kann man z. B. durch Hydrierung von substituierten Abkömmlingen des Amino-6-methyl-2-heptens-(2) die entsprechenden Abkömmlinge des Amino-6-methyl-2-heptans erhalten.So you can z. B. by hydrogenation of substituted descendants des amino-6-methyl-2-heptene- (2) the corresponding derivatives of amino-6-methyl-2-heptane obtain.
Man kann aber auch von "Ausgangsstoffen ausgehen, die zwei und mehr Doppelbindungen enthalten, wobei diese zwei oder mehr Doppelbindungen sowohl in einem R als auch in mehreren R enthalten sein können. So kann man z. B. von Verbindungen der allgemeinen Formeln ausgehen. In diesen Formeln haben R'1, R'2 und R'3 die bereits angegebene Bedeutung.However, one can also start from “starting materials which contain two or more double bonds, it being possible for these two or more double bonds to be contained in one R as well as in several R.sup. For example, compounds of the general formulas go out. In these formulas, R'1, R'2 and R'3 have the meanings already given.
Die Hydrierung erfolgt in bekannter Weise mit Wasserstoff in Gegenwart der üblichen Hydrierungskatalysatoren, wie Platin-, Nickel- und Kobaltkatalysatoren.The hydrogenation is carried out in a known manner with hydrogen in the presence the usual hydrogenation catalysts, such as platinum, nickel and cobalt catalysts.
In den Patentschriften 617536 und 617596 sind Verfahren zur Herstellung von ungesättigten Aminen vom Typus des Methylaminomethylheptens beschrieben worden, Verbindungen, die sich durch krampflösende Wirkung auszeichnen. Es war jedoch nicht vorauszusehen, daß auch gesättigte Amine, die Abkömmlinge des Äthylamins sind, wertvolle krampflösende Eigenschaften aufweisen würden. Ebensowenig war zu erwarten, daß die erfindungsgemäß hergestellten Verbindungen die erwähnten ungesättigten Amine in ihrer Wirkung auf die glatte Muskulatur zum Teil sogar übertreffen.In patents 617536 and 617596 are methods of manufacture of unsaturated amines of the methylaminomethylheptene type have been described, Compounds that are characterized by antispasmodic properties. However, it wasn't to foresee that saturated amines, which are derivatives of ethylamine, will also be valuable would have antispasmodic properties. Nor was it to be expected that the compounds prepared according to the invention include the unsaturated amines mentioned in in some cases even exceed their effect on the smooth muscles.
Ein weiterer nicht zu unterschätzender Vorzug der gesättigten Basen ist ihre größere Widerstandsfähigkeit gegenüber chemischen Einflüssen, wodurch nicht nur ihre technische Herstellung, sondern auch die Herstellung von beständigen Salzen wesentlich vereinfacht wird.Another advantage of saturated bases that should not be underestimated is their greater resistance to chemical influences, which does not only their technical production, but also the production of permanent salts is simplified significantly.
Beispiel i 7o,6 g Methylamino-6-methyl-2-hepten-2, C3 Hl, N, hergestellt durch Reduktion von Methyl-2-hepten-2-on-6 in Gegenwart von Methylamin, werden in Gegenwart von Wasserstoff und 2o g Nickelkatalysator bei einer Temperatur von 15ö bis 16o° im geschlossenen Gefäß der katalytischen Hydrierung unterworfen. Die Aufarbeitung erfolgt nach üblichen Verfahren.Example i 7o, 6 g of methylamino-6-methyl-2-hepten-2, C3 Hl, N, prepared by reducing methyl-2-hepten-2-one-6 in the presence of methylamine, are in Presence of hydrogen and 20 g of nickel catalyst at a temperature of 150 Subject to catalytic hydrogenation up to 16o ° in a closed vessel. The work-up takes place according to the usual procedures.
Das Methylamino-6-methyl-2-heptan, Cg H"N, siedet bei 62 bis 63° unter io mm Druck. Das Bitartrat kristallisiert aus Alkohol-Äther in Prismen vom F. 84 bis 86°. Ausbeute 7o bis 8o °/o der Theorie. Beispiel e 34 g Methylamino-5-hexeu-i, C7 H, N, hergestellt durch Reduktion von Hexen-i-on-5 in Gegenwart von. Methylamin, werden in der berechneten Menge verdünnter Salzsäure gelöst und in Gegenwart von Wasserstoff und ioo ccm i°/oiger kolloidaler Platinlösung katalytisch reduziert. Nach kurzer Zeit ist die berechnete Menge HZ aufgenommen. Die Aufarbeitung erfolgt in bekannter Weise.The methylamino-6-methyl-2-heptane, Cg H "N, boils below at 62 to 63 ° io mm pressure. The bitartrate crystallizes from alcohol-ether in prisms from F. 84 up to 86 °. Yield 70 to 80 percent of theory. Example e 34 g of methylamino-5-hexeu-i, C7 H, N, prepared by reducing hexen-i-one-5 in the presence of. Methylamine, are dissolved in the calculated amount of dilute hydrochloric acid and in the presence of Hydrogen and 100 cc of 100% colloidal platinum solution were catalytically reduced. After a short time, the calculated amount of HZ is absorbed. The work-up takes place in a known way.
Das Methylamino-5-hexan, C,H17N, siedet bei 132 bis 134° unter gewöhnlichem Druck und ist eine leicht bewegliche Flüssigkeit von stark ammoniakalischem Geruch. Ausbeute 7o bis 8o"/() der Theorie. Beispiel 3 36,z g Cyclohexylamino-5-hexen-i, C"H"N, hergestellt durch Reduktion von Hexen-i-on-5 in Gegenwart von Cyclohexamin, werden nach Beispiel e katalytisch hydriert und aufgearbeitet.Methylamino-5-hexane, C, H17N, boils at 132 to 134 ° under normal pressure and is an easily mobile liquid with a strong ammoniacal odor. Yield 70 to 80 "/ () of theory. Example 3 36, zg cyclohexylamino-5-hexen-i, C" H "N, prepared by reducing hexen-i-one-5 in the presence of cyclohexamine, are according to Example e catalytically hydrogenated and worked up.
Das Cyclohexylamino-5-hexan, C"H2"N, siedet bei 228° unter gewöhnlichem Druck. Das Chlorhydrat schmilzt bei 157 bis 158°.The cyclohexylamino-5-hexane, C "H2" N, boils at 228 ° below normal Pressure. The chlorohydrate melts at 157 to 158 °.
Beispiel 4 20,3 g N-Methyl benzylamino-5-hexen-i, hergestellt aus Methylamino-5-hexen-i und Benzylhalogenid, werden nach Beispiel 2 katalytisch hydriert und das Reaktionsgemisch in bekannter Weise aufgearbeitet.Example 4 20.3 g of N-methylbenzylamino-5-hexen-i, prepared from methylamino-5-hexen-i and benzyl halide, are catalytically hydrogenated according to Example 2 and the reaction mixture is worked up in a known manner.
Das N-Methyl-benzylamino-5-hexan siedet bei 254 bis 256° unter gewöhnlichem Druck. Das Oxalat ist ein kristallines Pulver vom F.122°. Ausbeute 7o bis 8o °/o der Theorie.The N-methyl-benzylamino-5-hexane boils at 254 to 256 ° below normal Pressure. The oxalate is a crystalline powder with a temperature of 122 °. Yield 70 to 80 per cent the theory.
Beispiel s 16,7 g Allylamino-6-methyl-2-hepten-2,C" H21 N,hergestellt durch Reduktion von Methyl-2-hepten-2-on-6 in Gegenwart von Allylamin, werden nach Beispiel 2 mit 40 ccm i o/oiger kolloidaler Platinlösung in Gegenwart von Wasserstoff katalytisch hydriert. Es erfolgt eine glatte Wasserstoffaufnahme in kurzer Zeit. Die Aufarbeitung geschieht in bekannter Weise.Example s 16.7 g of allylamino-6-methyl-2-hepten-2, C "H21 N, prepared by reduction of methyl-2-hepten-2-one-6 in the presence of allylamine, are according to Example 2 with 40 ccm of i o / o colloidal platinum solution in the presence catalytically hydrogenated by hydrogen. There is a smooth absorption of hydrogen in a short time. The work-up is done in a known manner.
Das Propylamino-6-methyl-2-heptan, C11H2,N, siedet bei 77° unter g mm Druck. Das Chlorhydrat kristallisiert aus Alkohol-Äther in kleinen Prismen vom F. r38°. Ausbeute 8o bis go °/o der Theorie.The propylamino-6-methyl-2-heptane, C11H2, N, boils at 77 ° below g mm pressure. The chlorine hydrate crystallizes from alcohol-ether in small prisms from F. r38 °. Yield 80 to 20% of theory.
Beispiel 6 36,2 g (N-Methyl-allylamino)-6-methyl-2-hepten-2, C12H23N, hergestellt aus iWethylamino-6-methyl-2-hepten-2 und Allylhalogenid, werden nach Beispiel 2 mit 8o ccm io/oiger kolloidaler Platinlösung katalytisch hydriert. Die Aufarbeitung erfolgt in gleicher Weise.Example 6 36.2 g (N-methyl-allylamino) -6-methyl-2-hepten-2, C12H23N, made from iWethylamino-6-methyl-2-hepten-2 and allyl halide, are according to Example 2 catalytically hydrogenated with 80 ccm 10 / o colloidal platinum solution. the Work-up takes place in the same way.
Das (N-Methyl-propylamino)-6-methyl-2-heptan, C12H27N, siedet bei 197 bis igg° unter gewöhnlichem Druck. Das Oxalat kristallisiert aus Alkohol-Äther in feinen Prismen vom F. 85 bis 87°. Ausbeute 8o °/o der Theorie.The (N-methyl-propylamino) -6-methyl-2-heptane, C12H27N, is boiling 197 to igg ° under ordinary pressure. The oxalate crystallizes from alcohol-ether in fine prisms from 85 to 87 °. Yield 80% of theory.
Beispiel 7 23,79 (Methyl-2-hepten-2-yl-6-amino)-6-methyl-2-hepten-2, C1oH31N, hergestellt durch Reduktion von Methyl-2-hepten-2-on-6 in Gegenwart von Amino-6-methyl-2-hepten-2, werden in Äther gelöst und nach Beispiel 2 der katalytischen Hydrierung unterworfen.Example 7 23.79 (methyl-2-hepten-2-yl-6-amino) -6-methyl-2-hepten-2, C1oH31N, prepared by reducing methyl-2-hepten-2-one-6 in the presence of amino-6-methyl-2-hepten-2, are dissolved in ether and subjected to catalytic hydrogenation according to Example 2.
Das (Methyl-2-heptyl-6-amino)-6-methyl-2-heptan, C"H"N, siedet bei 256 bis 258°. Ausbeute 7o bis 8o0/, der Theorie. Das in Wasser wenig lösliche Chlorhydrat kristallisiert in farblosen, fettig glänzenden Blättchen vom F. i47°.The (methyl-2-heptyl-6-amino) -6-methyl-2-heptane, C "H" N, boils off 256 to 258 °. Yield 7o to 8o0 /, of theory. The hydrate of chlorine, which is sparingly soluble in water crystallizes in colorless, greasy, shiny leaflets with a temperature of 47 °.
Beispiel 8 20,9 g Diallylamino-6-methyl-2-heptan, C14H27N, hergestellt aus Allylamino-6-methyl-2-heptan und Allylhalogenid, werden nach Beispiel 2 mit 40 ccm i °/oiger kolloidaler Platinlösung in Gegenwart von Wasserstoff katalytisch hydriert. Die Aufarbeitung geschieht in bekannter Weise. Das Dipropylamino-6-methyl-2-heptan, C14 H31 N, siedet bei 215 bis 2r8°. Ausbeute 7o-bis 8o')/, der Theorie.EXAMPLE 8 20.9 g of diallylamino-6-methyl-2-heptane, C14H27N, produced from allylamino-6-methyl-2-heptane and allyl halide, are catalytic according to Example 2 with 40 cc i% colloidal platinum solution in the presence of hydrogen hydrogenated. The work-up is done in a known manner. Dipropylamino-6-methyl-2-heptane, C14 H31 N, boils at 215 to 28 °. Yield 7o to 8o ') /, of theory.
Beispiel g 2o,7 g Diallylamino-6-methyl-2-hepten-2, C14H25N, hergestellt aus Allylamino-6-methyl-2-hepten-2 und Allylhalogenid, werden nach Beispiel 2 mit 6o ccm i %iger kolloidaler Platinlösung in Gegenwart von Wasserstoff hydriert. Die reduzierende Base wird in der üblichen Weise isoliert.Example g 2o, 7 g diallylamino-6-methyl-2-hepten-2, C14H25N, prepared from allylamino-6-methyl-2-hepten-2 and allyl halide, according to Example 2 with 60 cc i% colloidal platinum solution hydrogenated in the presence of hydrogen. the reducing base is isolated in the usual way.
Das Dipropylamino-6-methyl-2-heptan, C14H31N, ist mit der im Beispiel 8 beschriebenen Base identisch. Ausbeute 7o bis 8o °/o der Theorie.The dipropylamino-6-methyl-2-heptane, C14H31N, is the same as in the example 8 identical base described. Yield 70 to 80 percent of theory.
Claims (2)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK2793D DE874909C (en) | 1938-02-01 | 1938-02-01 | Process for the preparation of saturated derivatives of ethylamine |
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| Application Number | Priority Date | Filing Date | Title |
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| DEK2793D DE874909C (en) | 1938-02-01 | 1938-02-01 | Process for the preparation of saturated derivatives of ethylamine |
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| DE874909C true DE874909C (en) | 1953-04-27 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287410A (en) * | 1963-04-22 | 1966-11-22 | Millmaster Onyx Corp | Method of preparing aliphatic amines |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE617596C (en) * | 1931-12-16 | 1935-08-26 | Knoll Ag | Process for the preparation of secondary and tertiary unsaturated amines |
| DE617536C (en) * | 1931-07-02 | 1935-08-26 | Knoll Ag | Process for the preparation of unsaturated amines |
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1938
- 1938-02-01 DE DEK2793D patent/DE874909C/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE617536C (en) * | 1931-07-02 | 1935-08-26 | Knoll Ag | Process for the preparation of unsaturated amines |
| DE617596C (en) * | 1931-12-16 | 1935-08-26 | Knoll Ag | Process for the preparation of secondary and tertiary unsaturated amines |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287410A (en) * | 1963-04-22 | 1966-11-22 | Millmaster Onyx Corp | Method of preparing aliphatic amines |
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