CS208855B1 - N- [4- (2-naphthyloxy) butyl] amines and methods for their preparation - Google Patents
N- [4- (2-naphthyloxy) butyl] amines and methods for their preparation Download PDFInfo
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- CS208855B1 CS208855B1 CS35879A CS35879A CS208855B1 CS 208855 B1 CS208855 B1 CS 208855B1 CS 35879 A CS35879 A CS 35879A CS 35879 A CS35879 A CS 35879A CS 208855 B1 CS208855 B1 CS 208855B1
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- naphthyloxy
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
a. b. c. a. e. N-(4-/2-naftyloxy/butyl)amíny a spo sob ich přípravy Organická chémla Syntéza Syntéza N-(4-/2-naftyloxy/butyl)amínov z l-bróm-4-/2-naftyloxy/butánu a nasýteného heterocykllckého sekun dárného aminu za přítomnosti bezvo dého uhličitanu draselného. Finálně zlúčeniny slúžia aKo medziprodukty pri príprsve biologicky účinných zlúčenín. Farmaceutický, chemický, vláknársky priemysel, kozmetika.a. b. c. a. e. N-(4-/2-naphthyloxy/butyl)amines and methods of their preparation Organic chemistry Synthesis Synthesis of N-(4-/2-naphthyloxy/butyl)amines from 1-bromo-4-/2-naphthyloxy/butane and a saturated heterocyclic secondary amine in the presence of anhydrous potassium carbonate. Finally, the compounds serve as intermediates in the synthesis of biologically active compounds. Pharmaceutical, chemical, fiber industry, cosmetics.
Description
Vynález sa týka N-(*4-/2-naftyloxy/butyl)amínov obecného vzorca
kde X značí /CHg/^ ag 7 a /CH2CH2/20 , a spôsobu ich prípravy. Ako je známe, mnohé deriváty nasýtených heterocyklických amínov výkazujú výrazné biologické účinky. Zlúčeniny, ktorých molekula obsahuje amínovú zložku a súčasne cez éterickú väzbu viazaný naftaléno-vý skelet, však doteraz neboli pripravené, ani sledované z hľadiska ich biologických účinkov. Zlúčeniny, ktoré sú podstatou vynálezu sú látky nové, doteraz v literatúre neopísané a slúžia ako východiskové suroviny pri príprave nových antimikrobiálne účinných látok.
Nové zlúčeniny sa pripravujú spôsobom podľa vynálezu, ktorého podstatou je reakcia l-brom-4-/2-naftyloxy/butánu s príslušným nasýteným heterocyklickým amínom za prítomnosti bezvodého uhličitanu draselného pri teplote 150 °C počas 1,5 hodiny.
Na ilustráciu vyššie uvedených zlúčenín a spôsobu ich prípravy sú uvedené nasledovné príklady.
Príklad 1
Zmes 19 g bezvodého uhličitanu draselného, 41,9 g l-bróm-4-/2-naftyloxy/butánu a 21,3 g pyrolidínu sa nechá reagovať počas 1,5 hodiny pri teplote 150 °C. Po ochladení sa pevné podiely rozpustia vo vode a produkt sa extrahuje. Extrakty sa vysušia, rozpúšlfe dlo sa oddestiluje a produkt s,a frakčne predestlluje. Výťažok N-(4-/2-naftylosy/butyl)pyrolidínu je 88 %; t.v. 201 až 203 °C pri tlaku 0,08 kPaj t.t. 47 °Cj elementárna analýza /vypočítané/nájdené %/s 080,26/80,10, H«8,6l/8,50, N=5,2O/5,O2.
Príklad 2
Pracovný postup je ten istý.ako v príklade 1, namiesto pyrolidínu sa použil morfolín. Výťažok N-(4_/2-naŕtyloxy/butyl)morfolínu je 89 %i t.v. 215 až 217 °C /0,05 kPa; n^=l,5735i elementárna analýza /vypočítané/nájdené %/ i 0=75,76/75,67, H=8,12/8,40, 04,91/5,08. ,
Príklad 3
Pracovný postup je ten istý ako v príklade 1, namiesto pyrolidínu sa použil perhydro-azepín. Výťažok N-(4-/2-naŕtyloxy/butyl)perhydroazepínu je 87 %» t.v. 203 °C/0,05 kPaj n^>“l,5722j elementárna analýza /vypočítanó/nájdené %/1 0=80,76/80,90, H=9,15/9,4O, W,71/4,87.
The invention relates to N - (* 4- (2-naphthyloxy) butyl) amines of the general formula
wherein X is (CH 3) 2 and 7 and / CH 2 CH 2/20, and a method for preparing the same. As is known, many saturated heterocyclic amine derivatives exhibit significant biological effects. However, the compounds whose molecule contains the amine component and the naphthalene skeleton bound via the ether bond have not yet been prepared or monitored for their biological effects. The compounds of the invention are novel substances not previously described in the literature and serve as starting materials in the preparation of novel antimicrobial active substances.
The novel compounds are prepared by the process of the invention, which is based on the reaction of 1-bromo-4- (2-naphthyloxy) butane with an appropriate saturated heterocyclic amine in the presence of anhydrous potassium carbonate at 150 ° C for 1.5 hours.
The following examples are provided to illustrate the above compounds and their method of preparation.
Example 1
A mixture of 19 g of anhydrous potassium carbonate, 41.9 g of 1-bromo-4- (2-naphthyloxy) butane and 21.3 g of pyrrolidine was reacted for 1.5 hours at 150 ° C. After cooling, the solids are dissolved in water and the product is extracted. The extracts are dried, the solvent is distilled off, and the product is fractionated. The yield of N- (4- (2-naphthyl) butyl) pyrrolidine is 88%; t 201 to 203 ° C at 0.08 kPa tt 47 ° C elemental analysis (calculated / found% / s 080.26 / 80.10, H «8.6l / 8.50, N = 5.2O / 5) , O2.
Example 2
The working procedure is the same as in Example 1, using morpholine instead of pyrrolidine. The yield of N- (4- (2-naphthyloxy) butyl) morpholine was 89% and 215-217 ° C / 0.05 kPa; n = 1, 5735i elemental analysis (calculated / found%) = 75.76 / 75.67, H = 8.12 / 8.40, 04.91 / 5.08. ,
Example 3
The working procedure is the same as in Example 1, instead of pyrrolidine perhydroazepine was used. The yield of N- (4- (2-naphthyloxy) butyl) perhydroazepine is 87%? Tv 203 ° C / 0.05 kPaj n?>? 5722? Elemental analysis / calculated / found% / 10 = 80.76 / 80 , 90, H = 9.15 / 9.4O, W, 71 / 4.87.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS35879A CS208855B1 (en) | 1979-01-17 | 1979-01-17 | N- [4- (2-naphthyloxy) butyl] amines and methods for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS35879A CS208855B1 (en) | 1979-01-17 | 1979-01-17 | N- [4- (2-naphthyloxy) butyl] amines and methods for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS208855B1 true CS208855B1 (en) | 1981-10-30 |
Family
ID=5335517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS35879A CS208855B1 (en) | 1979-01-17 | 1979-01-17 | N- [4- (2-naphthyloxy) butyl] amines and methods for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS208855B1 (en) |
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1979
- 1979-01-17 CS CS35879A patent/CS208855B1/en unknown
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