CS200146B1 - N-/omega-phenoxyalkyl/piperidin-n-oxides and process for preparing thereof - Google Patents
N-/omega-phenoxyalkyl/piperidin-n-oxides and process for preparing thereof Download PDFInfo
- Publication number
- CS200146B1 CS200146B1 CS36179A CS36179A CS200146B1 CS 200146 B1 CS200146 B1 CS 200146B1 CS 36179 A CS36179 A CS 36179A CS 36179 A CS36179 A CS 36179A CS 200146 B1 CS200146 B1 CS 200146B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenoxyalkyl
- oxides
- piperidine
- piperidin
- omega
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 3
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 claims description 3
- 150000003053 piperidines Chemical class 0.000 claims 1
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- -1 ozene Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RSUFKEGMFFPMIB-UHFFFAOYSA-N 1-(2-phenoxyethyl)piperidine Chemical compound C=1C=CC=CC=1OCCN1CCCCC1 RSUFKEGMFFPMIB-UHFFFAOYSA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003327 cancerostatic effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000004680 hydrogen peroxides Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
Description
(54) N-(<n-fenoxyalkyl) piperidln-N-oxidy a sp&eob ich přípravy( 54 ) N - (<n -phenoxyalkyl) piperidine-N-oxides and methods for their preparation
Vynález sa týká. N-(cj-fenoxyalkyl)piperidín-N-oxidov obeeného vzorca.The invention relates. N- (C 1 -phenoxyalkyl) piperidine-N -oxides of the formula.
kde n značí 2 až 10, a sp&sobu ich přípravy. V súčasnosti majú asiínoxidy váaka niektorým svojim výhodným vlastnostiam široká využitie v priemysle. Používajú sa ako detergenčné, povrchovoaktívne látky, antioxidapty, dezinficienciá, kancerostatiká apod.. Zlúčeniny, ktoré sú podstatou vynálezu, aú nové, doteraz v literatúre neoplsané a zistili aa u nich doteraz neznáme účinky na niektoré kmene mikroorganizmev. Tento antimikrobiálny účinok bol vyšší alebo zrovnatelný s preparútmi typu améniových soli používanými v súčasnosti u nás.wherein n denotes 2 to 10, and a process for their preparation. Currently, some of its advantageous properties of vacuum asine oxides are widely used in industry. They are used as detergents, surfactants, antioxidants, disinfectants, carcinostatics and the like. The compounds of the present invention are novel and have not been disclosed in the literature yet and have found and yet unknown effects on certain microorganism strains. This antimicrobial effect was higher or comparable to the amenium salt formulations currently used in our country.
Ako je z literatúry známe, dajú sa amínoxidy pripraviť niekolkými spAsobmi /oxidáciou kyselinou Carovou, ozénom, hydrogénporoxidmi za katalýzy soli kovov, peroxidem vodíka apod./ Oxidácia má oproti iným sp&sobom přípravy amínoxidov tú výhodu, že vznikajú produkty vo vyaokom výtažku, vysokej čistoty, za použitia len malého množstva rozpúšťadla a reakčni doba je v porovnaní a inými metédami přípravy amínoxidov podstatné kratšia.As is known in the literature, amine oxides can be prepared in several ways / by oxidation with carboxylic acid, ozene, hydrogen peroxides under the catalysis of metal salts, hydrogen peroxide, etc./ Oxidation has the advantage over other methods of preparation of amine oxides using only a small amount of solvent and the reaction time is considerably shorter compared to other amine oxide preparation methods.
Nové zlúčeniny sa prlpravujú sp&sobom podía vynálezu, ktorého podstatou je, žo sa oxiduje příslušný terciárny amin N-(u>-fenoxýalkyl)piperidin 30 % vodným roztokom peroxidu vodíkav metanole pri teplote 60 °C počas 3 hodin.The novel compounds are prepared according to the invention by oxidizing the corresponding tertiary amine N- (n-phenoxyalkyl) piperidine with a 30% aqueous solution of hydrogen peroxide and methanol at 60 ° C for 3 hours.
200 146200 146
200 148200 148
Ka ilustráciu spdsobu přípravy ako i niektorých fyzikálnych konfitát sú uvedené následovně příklady.The following examples are given to illustrate the preparation method as well as some physical confitates.
Přiklad 1Example 1
V 20 mi metanolu sa rozpustí 0,1 mol N-(2-fenoxyetyl)piperidínu, zahřeje sa na 80 °C a pri tejto teplote ea přidá 0,12 mel 30% vodného roztoku peroxidu vodíka. Reakčná zmes sa nechá doreagovať ešte 3 hodiny. Po ochladeni, rozložení prebytočného peroxidu vodíka, odpa roní vody a 'rozpúšťadla sa surový produkt prekryStalizujo niekoíko krát do konfitantnej teploty topenia· Výťažok K-(2-fenoxyetyl)piperidín-N-oxidu je 79 %, t.t. 140 až 143 °C, elementárna analýza (vypočltané/nájderié 070,56/69,95, 08,65/8,89, 06,33/6,25, λ „ =219,270 nm.Dissolve 0.1 mol of N- (2-phenoxyethyl) piperidine in 20 ml of methanol, heat to 80 ° C and add 0.12 ml of a 30% aqueous hydrogen peroxide solution at this temperature e. The reaction mixture was allowed to react for a further 3 hours. After cooling, decomposition of excess hydrogen peroxide, evaporation of water and solvent, the crude product is recrystallized several times to a confident melting point. The yield of K- (2-phenoxyethyl) piperidine-N-oxide is 79%, m.p. 140-143 ° C, elemental analysis (calculated / found 070.56 / 69.95, 08.65 / 8.89, 06.33 / 6.25, λ "= 219.270 nm).
. na* ,. on* ,
Příklad 2Example 2
Pracovný postup je ten istý ako v přiklade 1, na oxidáeiu sa však použil K-(5-fenoxypentyl)piperidín. Výťažok produktu je 86 %, t.t. 166 až 169 °C, elementárna analýza (vypočítané/nájdené %): 072,97/72,64, 09,57/9,58, 05,32/5,09^^^221,271 nm.The procedure is the same as in Example 1, but K- (5-phenoxypentyl) piperidine was used for the oxidation. The product yield is 86%, m.p. 166-169 ° C, elemental analysis (calculated / found%): 072.97 / 72.64, 09.57 / 9.58, 05.32 / 5.09.
Příklad 3Example 3
Pracovný postup je ten istý ako v příklade 1, na oxidáeiu sa vfiak použil K-(8-fenoxyoktyl{piperidín. Výťažok produktu je 86 %, t.t. 117 až 120 °C, elementárna analýza (vypočl tané/nájdené %): 074,71/74,22, 010,23/9,98, 04,59/4,51, λ«220,271 nm.The procedure is the same as in Example 1 except that K- (8-phenoxyoctyl {piperidine) is used for the oxidation, yield 86%, mp 117-120 ° C, elemental analysis (calculated / found%): 074.71 (74.22, 010.23 / 9.98, 04.59 / 4.51, λ 220.271 nm).
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS36179A CS200146B1 (en) | 1979-01-17 | 1979-01-17 | N-/omega-phenoxyalkyl/piperidin-n-oxides and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS36179A CS200146B1 (en) | 1979-01-17 | 1979-01-17 | N-/omega-phenoxyalkyl/piperidin-n-oxides and process for preparing thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200146B1 true CS200146B1 (en) | 1980-08-29 |
Family
ID=5335551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS36179A CS200146B1 (en) | 1979-01-17 | 1979-01-17 | N-/omega-phenoxyalkyl/piperidin-n-oxides and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS200146B1 (en) |
-
1979
- 1979-01-17 CS CS36179A patent/CS200146B1/en unknown
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