CH176830A - Process for the preparation of a cyclic amine. - Google Patents
Process for the preparation of a cyclic amine.Info
- Publication number
- CH176830A CH176830A CH176830DA CH176830A CH 176830 A CH176830 A CH 176830A CH 176830D A CH176830D A CH 176830DA CH 176830 A CH176830 A CH 176830A
- Authority
- CH
- Switzerland
- Prior art keywords
- cyclic amine
- reduction
- carried out
- preparation
- sodium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- -1 cyclic amine Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 230000001766 physiological effect Effects 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- KBQDZEMXPBDNGH-UHFFFAOYSA-N cycloheptadecanone Chemical compound O=C1CCCCCCCCCCCCCCCC1 KBQDZEMXPBDNGH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QNTADTGUHSAVOZ-UHFFFAOYSA-N 17-aminoheptadecanoic acid Chemical compound NCCCCCCCCCCCCCCCCC(O)=O QNTADTGUHSAVOZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SUEFPLOYVGKMSD-UHFFFAOYSA-N n-cycloheptadecylidenehydroxylamine Chemical compound ON=C1CCCCCCCCCCCCCCCC1 SUEFPLOYVGKMSD-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines cyclischen Amins. Es wurde gefunden, dass man zu einem cyclischen Amin gelangen kann, wenn man auf Cycloheptadecanon-thioisoxim (Lactam der 17-Amino-heptadecanthionsäure) ein Re duktionsmittel einwirken lässt.
Das auf diese Weise erhaltene Hepta- decamethylenimin der Formel
EMI0001.0008
schmilzt bei<B>64-66.</B>
Das neue Amin zeichnet sich durch seine physiologische Wirkung aus und soll thera peutische Verwertung finden. Beispiel <I>;</I> 1 Gewichtsteil Cycloheptadecanonoxim wird mit 2-3 Gewichtsteilen starker Schwe felsäure, hergestellt durch Mischen von 4 Raumteilen konzentrierter Schwefelsäure und 1 Raumteil Wasser, über freier Flamme er hitzt. Sobald die anfänglich rotorange Farbe der Lösung in braun übergegangen ist, wird auf Eis gegossen, das Reaktionsprodukt mit Äther ausgezogen und aus Aceton umkristal lisiert. Das. Cycloheptadecanon-isoxim (Lactam der 17-Amino-heptadecansäure schmilzt bei 124-1250.
Ein Gewichtsteil des Isoxims wird in 10 Raumteilen gylol gelöst und unter Rühren mit der Turbine mit 0,9 Gewichtsteilen Phos- phorpentasulfid versetzt. Das Gemisch erhitzt man allmählich auf 100 und lässt es 2 Stun den bei dieser Temperatur. Man fügt dann Natronlauge zu und erhitzt weiter, bis alles in Lösung geht. Nach Abtrennung der Xylol- schicht und Verdampfung des Lösungsmittels wird der Rückstand aus Benzin umkristalli siert. Das erhaltene Cycloheptadecanon-thio- isoxim schmilzt bei 110-1110.
1 Gewichtsteil Thioisoxim wird in der 40-fachen Menge absolutem Alkohol gelöst, mit der 17-fachen Menge Eisessig versetzt und dann dazu unter starkem Sieden und kräftigem Rühren die 6-fache Menge Natrium eingetragen. Der Alkohol wird dann im Va- kuum abdestilliert und der Rückstand in Wasser aufgelöst: Die wässerige Lösung scheidet beim Übersättigen mit Lauge das Heptadecamethylenimin ab. Es wird im Va kuum destilliert und erstarrt beim Erkalten.
Die Reduktion des Thioisogims kann beispielsweise auch auf elektrolytischem Wege vorgenommen werden.
Process for the preparation of a cyclic amine. It has been found that a cyclic amine can be obtained if a reducing agent is allowed to act on cycloheptadecanone thioisoxime (lactam of 17-amino-heptadecanthionic acid).
The heptadecamethyleneimine of the formula obtained in this way
EMI0001.0008
melts at <B> 64-66. </B>
The new amine is characterized by its physiological effect and should be used therapeutically. Example <I>; </I> 1 part by weight of cycloheptadecanone oxime is heated with 2-3 parts by weight of strong sulfuric acid, prepared by mixing 4 parts by volume of concentrated sulfuric acid and 1 part by volume of water, over a free flame. As soon as the initially red-orange color of the solution has turned brown, it is poured onto ice, the reaction product extracted with ether and recrystallized from acetone. The. Cycloheptadecanone isoxime (lactam of 17-amino-heptadecanoic acid melts at 124-1250.
One part by weight of the isoxime is dissolved in 10 parts by volume of gylene and 0.9 parts by weight of phosphorus pentasulphide are added while stirring with the turbine. The mixture is gradually heated to 100 and left for 2 hours at this temperature. Sodium hydroxide solution is then added and heating continues until everything goes into solution. After the xylene layer has been separated off and the solvent has evaporated, the residue is recrystallized from gasoline. The cycloheptadecanone-thio-isoxime obtained melts at 110-1110.
1 part by weight of thioisoxime is dissolved in 40 times the amount of absolute alcohol, 17 times the amount of glacial acetic acid is added, and 6 times the amount of sodium is then added with vigorous boiling and vigorous stirring. The alcohol is then distilled off in vacuo and the residue is dissolved in water: the aqueous solution separates the heptadecamethyleneimine when it is oversaturated with lye. It is distilled in a vacuum and solidifies when it cools.
The thioisogime can also be reduced, for example, by electrolytic means.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH172873T | 1933-08-22 | ||
| CH176830T | 1933-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH176830A true CH176830A (en) | 1935-04-30 |
Family
ID=25719290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH176830D CH176830A (en) | 1933-08-22 | 1933-08-22 | Process for the preparation of a cyclic amine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH176830A (en) |
-
1933
- 1933-08-22 CH CH176830D patent/CH176830A/en unknown
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