CS209355B1 - N- (4- [1-naphthyloxy] butyl) amines and their method of preparation - Google Patents

N- (4- [1-naphthyloxy] butyl) amines and their method of preparation Download PDF

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CS209355B1
CS209355B1 CS35979A CS35979A CS209355B1 CS 209355 B1 CS209355 B1 CS 209355B1 CS 35979 A CS35979 A CS 35979A CS 35979 A CS35979 A CS 35979A CS 209355 B1 CS209355 B1 CS 209355B1
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naphthyloxy
butyl
preparation
amines
pyrrolidine
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CS35979A
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Czech (cs)
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Ferdinand Devinsky
Ivan Lacko
Ludovit Krasnec
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Ferdinand Devinsky
Ivan Lacko
Ludovit Krasnec
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Priority to CS35979A priority Critical patent/CS209355B1/en
Publication of CS209355B1 publication Critical patent/CS209355B1/en

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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Syntéza N-(4-[í-naftyloxy]butyl)amínov z *1- -bróm-4-(l-naftyloxy)butánu z nasýteného heterocyklického sekundárného aminu za pomoci bezvodého uhličitanu draselného. Finálně zlúčeniny slúžia ako medziprodukty pre přípravu biologicky účinných zlúčenín.Synthesis of N-(4-[1-naphthyloxy]butyl)amines from *1-bromo-4-(1-naphthyloxy)butane from a saturated heterocyclic secondary amine with the aid of anhydrous potassium carbonate. Finally, the compounds serve as intermediates for the preparation of biologically active compounds.

Description

(54) N-(4-[l-naftyloxy]butyl)amíny a spósob ich přípravy(54) N- (4- [1-naphthyloxy] butyl) amines and processes for their preparation

Syntéza N-(4-[í-naftyloxy]butyl)amínov z *í-bróm-4-(l-naftyloxy)butánu z nasýteného heterocyklického sekundárného aminu za pomoci bezvodého uhličitanu draselného. Finálně zlúčeniny slúžia ako medziprodukty pre přípravu biologicky účinných zlúčenín.Synthesis of N- (4- [1-naphthyloxy] butyl) amines from 1'-bromo-4- (1-naphthyloxy) butane from saturated heterocyclic secondary amine with anhydrous potassium carbonate. Finally, the compounds serve as intermediates for the preparation of biologically active compounds.

Vynález sa týká N-(4-[l-naftyloxy]butyl)amínov obecného vzorcaThe invention relates to N- (4- [1-naphthyloxy] butyl) amines of the general formula

kde X značí (CH2)4 ÍEŽ 7 a (CH2CH2)2O a spósobu ich přípravy. Ako je známe, mnohé deriváty nasýtených heterocyklických amínov vykazujú výrazné biologické vlastnosti. Zlúčeniny, ktorých molekula obsahuje amínovú zložku a súčasne cez éterickú vazbu viazaný naftalénový skelet však doteraz neboli ani připravené ani sledované z hradiska ich biologických účinkov. Zlúčeniny, ktoré sú podstatou vynálezu, sú látky nové, doteraz v literatúre neopísané a slúžia ako východiskové suroviny pri přípravě nových antimikrobiálne účinných zlúčenín.wherein X denotes (CH 2 ) 4 E 7 and (CH 2 CH 2 ) 2 O and a process for their preparation. As is known, many derivatives of saturated heterocyclic amines exhibit significant biological properties. However, compounds whose molecule contains an amine moiety and at the same time an ether-bound naphthalene backbone have neither been prepared nor monitored for their biological effects. The compounds of the present invention are novel substances not previously described in the literature and serve as starting materials in the preparation of novel antimicrobially active compounds.

Nové zlúčeniny sa pripravujú spósobom podlá vynálezu, ktorého podstatou je reakcia l-bróm-4(l-naftyloxy)butánu s příslušným nasýteným heterocyklickým amínom za přítomnosti bezvodého uhličitanu draselného pri teplote 150 °C počas 1,5 hodiny. Výhodou tejto metody přípravy oprotiThe novel compounds are prepared according to the process of the invention, which comprises reacting 1-bromo-4- (1-naphthyloxy) butane with an appropriate saturated heterocyclic amine in the presence of anhydrous potassium carbonate at 150 ° C for 1.5 hours. The advantage of this method of preparation over

Claims (2)

PREDMETSUBJECT 1. N-(4-[l-naftyloxy]butyl)amíny obecného iným spósobom syntézy je vysoká výťažkovosť a čistota vznikajúcich produktov.1. N- (4- [1-naphthyloxy] butyl) amines in general Another method of synthesis is the high yield and purity of the resulting products. Na ilustráciu vyššie uvedených zlúčenín a spósobu ich přípravy sú uvedené následovně příklady.To illustrate the above compounds and methods for their preparation, the following examples are provided. Příklad 1Example 1 Zmes 19 g bezvodého uhličitanu draselného,Mixture of 19 g of anhydrous potassium carbonate, 41,9 g l-bróm-4-(l-naftyloxy)butánu a 21,3 g pyrolidínu sa nechá reagovat 1,5 h pri teplote 150 °C. Po ochladení a rozpuštění pevných podielov vo vodě sa produkt extrahuje. Extrakty sa vysušia, rozpúšťadlo sa oddestiluje a produkt sa predestiluje. N-(4-/l-naftyloxy/butyl)pyrolidín vzniká vo výtažku 84%; t. v. 187 °C/0,08 kPa; ηθ° = 1,5772; elementárna analýza (vypočítané/ nájdené %): C = 80,26/80,00, H = 8,61/8,82, N = 5,20/5,29; kmax = 212, 233, 296, 308, 322 nm.41.9 g of 1-bromo-4- (1-naphthyloxy) butane and 21.3 g of pyrrolidine are reacted for 1.5 hours at 150 ° C. After cooling and dissolving the solids in water, the product is extracted. The extracts are dried, the solvent is distilled off and the product is distilled off. N- (4- (1-naphthyloxy) butyl) pyrrolidine is obtained in 84% yield; t 187 ° C / 0.08 kPa; ηθ ° = 1.5772; Elemental Analysis (calculated / found%): C = 80.26 / 80.00, H = 8.61 / 8.82, N = 5.20 / 5.29; λ max = 212, 233, 296, 308, 322 nm. Příklad 2Example 2 Pracovný postup je ten istý ako v příklade 1, namiesto pyrolidínu sa však použil perhydroazepín. Výťažok N-(4-[l-naftyloxy]butyl)perhydroazepínu je 80%; t. v. 210 °C/0,08 kPa; ηθ° = 1,5550; elementárna analýza (vypočítané/ nájdené %): C = 80,76/80,85, H = 9,15/9,03, N = 4,71/4,60; ληι;ιχ = 211, 233, 295, 306, 322 nm.The procedure is the same as in Example 1, but perhydroazepine was used instead of pyrrolidine. The yield of N- (4- [1-naphthyloxy] butyl) perhydroazepine is 80%; tt 210 ° C / 0.08 kPa; ηθ ° = 1.5550; Elemental Analysis (calculated / found%): C = 80.76 / 80.85, H = 9.15 / 9.03, N = 4.71 / 4.60; λλ = 211, 233, 295, 306, 322 nm. VYNÁLEZU uhlíka v kruhu 4 až 7 alebo morfolín s l-bróm-4-(l-naftyloxy)butánom vzorca kde X značí (CH2)4 7 a (CH2CH2)2O.OF THE INVENTION carbon ring 4-7 or morpholine with 1-bromo-4- (1-naphthyloxy) butane of the formula wherein X is (CH 2 ) 4 7 and (CH 2 CH 2 ) 2 O. 2. Sposob přípravy zlúčenín podra bodu 1, vyznačujúci sa tým, že sa nechá reagovat nasýtený heterocyklický sekundárný amin s počtom atómov pri teplote 150 °C počas 1,5 hodiny za přítomnosti bezvodého uhličitanu draselného v prostředí bez rozpúšťadla.2. A process for the preparation of the compounds according to claim 1, which comprises reacting a saturated heterocyclic secondary amine with a number of atoms at 150 DEG C. for 1.5 hours in the presence of anhydrous potassium carbonate in a solvent-free environment.
CS35979A 1979-01-17 1979-01-17 N- (4- [1-naphthyloxy] butyl) amines and their method of preparation CS209355B1 (en)

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