CS200147B1 - N-/omega-phenoxyalkyl/piperidines and process for preparing them - Google Patents

N-/omega-phenoxyalkyl/piperidines and process for preparing them Download PDF

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Publication number
CS200147B1
CS200147B1 CS36279A CS36279A CS200147B1 CS 200147 B1 CS200147 B1 CS 200147B1 CS 36279 A CS36279 A CS 36279A CS 36279 A CS36279 A CS 36279A CS 200147 B1 CS200147 B1 CS 200147B1
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Czechoslovakia
Prior art keywords
bromo
piperidine
kpa
calculated
found
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CS36279A
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Czech (cs)
Slovak (sk)
Inventor
Ivan Lacko
Ferdinand Devinsky
Ludovit Krasnec
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Ivan Lacko
Ferdinand Devinsky
Ludovit Krasnec
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Application filed by Ivan Lacko, Ferdinand Devinsky, Ludovit Krasnec filed Critical Ivan Lacko
Priority to CS36279A priority Critical patent/CS200147B1/en
Publication of CS200147B1 publication Critical patent/CS200147B1/en

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Description

Vynález sa týká N-(u-fenoxyalkyl)piperidlnov obecného vzorca kde n značí 2 až 10, a spAsobu ioh přípravy. Ako je známe, niektoré deriváty piperidínu vykazujú biologické vlastnosti ako napr. hypotenzivny, lokálně anestetický, myorelaxačný, antiadrenolytický účinok apod.. Zlúčeniny, ktoré sú podstatou vynálezu, sú látky nové, doteraz v literatúre neoplsané. Slúžia ako východiskové suroviny pri príprave dalších biologicky aktívnych zlúčenín.The present invention relates to N- (u-phenoxyalkyl) piperidines of the general formula wherein n is from 2 to 10, and to a process for its preparation. As is known, some piperidine derivatives exhibit biological properties such as e.g. hypotensive, locally anesthetic, myorelaxant, antiadrenolytic, and the like. The compounds of the present invention are novel substances not yet described in the literature. They serve as starting materials in the preparation of other biologically active compounds.

Nové zlúčeniny sa pripravujú spAsobom podía vynálezu, ktorého podstatou je, že sa nechá reagovat l-brém-O-fenoxyalkán s piperidlnom v prostředí vriaceho benzénu počas 6 hodin.The novel compounds are prepared according to the process of the invention which comprises reacting 1-bromo-O-phenoxyalkane with piperidine in a boiling benzene medium for 6 hours.

Spésob podía vynálezu dává vysoké výtažky, čisté produkty a pracovný postup je jednoduchý.The process of the invention yields high yields, pure products and the process is simple.

'·'·

Na ilustráclu spAsobu přípravy ako i niektorých fyzikálnych konštánt sú uvedená následovně příklady.The following examples are given to illustrate the preparation process and some physical constants.

200 147200 147

200 147200 147

Příklad 1Example 1

K roztoku 0,2 mol piperldlnu v 200 ml benzénu sa za varu přidá 0,1 mol l-bróm-2-fenoxy etánu. Reakčná zmes sa udržuje ešte β hodin pri tejto teplote, po ochladeni a přefiltrováni sa rozpúšťadlo oddestiluje a produkt sa frakčně predestiluje. (2-fenoxyetyl)-piperidln vzniká vo výťažku 73 %; t.v. 105 až 110 °C/0,04 kPa; elementárna analýza, (vypočítané/ nájdené): 076,08/78,00, 09.33/9,40, 06,82/6,78.To a solution of 0.2 mol of piperidine in 200 ml of benzene was added boiling 0.1 mol of 1-bromo-2-phenoxy ethane. The reaction mixture is kept at this temperature for β hours, after cooling and filtration, the solvent is distilled off and the product is fractionally distilled off. (2-phenoxyethyl) -piperidine is produced in 73% yield; bp 105-110 ° C / 0.04 kPa; Elemental Analysis (calculated / found): 076.08 / 78.00, 09.33 / 9.40, 06.82 / 6.78.

Příklad 2Example 2

Pracovný postup je ten istý ako v přiklade 1, ako alkylačné činidlo aa však použil l-bróm-5-fenoxypentán. Produkt vzniká vo výťažku 76 %. t.v. 140 až 143 °C/0,05 kPa, element árna analýza (vypočítané/nájdené %): 077,68/77,76, 010,19/10,23 , 05,66/5,58.The procedure is the same as in Example 1 as the alkylating agent, but using 1-bromo-5-phenoxypentane. The product is obtained in a yield of 76%. bp 140-143 ° C / 0.05 kPa, elemental analysis (calculated / found%): 077.68 / 77.76, 010.19 / 10.23, 05.66 / 5.58.

Přiklad 3Example 3

Pracovný postup je ten istý ako v přiklade 1, ako alkylačné Činidlo aa použil 1-brám-8-fenoxyoktán. Produkt vzniká vo výťažku 78 %; t.v. 165 °C/0,04 kPa; elementárna analýza (vypočítané/nájdené %): OTO,84/78,96, 010,79/10,74 , 04,84/4,80.The procedure is the same as in Example 1 as the alkylating agent a and used 1-bromo-8-phenoxyoctane. The product is obtained in a yield of 78%; bp 165 ° C / 0.04 kPa; Elemental analysis (calculated / found%): OTO, 84 / 78.96, 010.79 / 10.74, 04.84 / 4.80.

Claims (2)

200 147 Příklad 1 K roztoku 0,2 mol piperidlnu v 200 ml benzénu sa za varu přídí 0,1 mol l-bróm-2-fenoxyetínu. Reakčná zmes sa udržuje ešte 6 hodin pri tejto teplotě, po ochladení a přefiltrova-ní sa rozpúšťadlo oddestiluje a produkt sa frakčne predeetiluje. K-(2-fenoxyetyl)-piperi-dín vzniká vo výtažku 73 %; t.v. 105 až 110 °C/0,04 kPa; elementárna analýza, (vypočítané/nájdené): 076,08/78,00, 09,33/9,40, 06,82/6,78. Příklad 2 Pracovný postup je ten istý ako v přiklade 1, ako alkylačné činidlo sa víak použill-brém-5-fenoxypentán. Produkt vzniká vo výtažku 76 X, t.v. 140 až 143 °C/0,05 kPa, ele-mentárna analýza (vypočítané/nájdené X): 077,68/77,76, 010,19/10,23 , 05,66/5,58. Přiklad 3 Pracovný postup je ten istý ako v příklade 1, ako alkylačné Činidlo aa použil 1-brdm--8-fenoxyoktán. Produkt vzniká vo výtažku 78 X; t.v. 165 °C/0,04 kPa; elementárna analýza(vypočítané/nájdené X): 078,84/78,96, 010,79/10,74 , 04,84/4,80. PREDMET VYNALEZU -¼ 1. K-(ω-fenoxyalkyl) píperidlny obecného vzorca O-^-Q kde n značí 2 až 10.EXAMPLE 1 To a solution of 0.2 mol of piperidine in 200 ml of benzene was added 0.1 mol of 1-bromo-2-phenoxyetine at boiling. The reaction mixture was maintained at this temperature for 6 hours, after which the solvent was distilled off after cooling and filtration, and the product was fractionally pre-distilled. K- (2-phenoxyethyl) piperidine is formed in 73% yield; t.v. 105-110 ° C / 0.04 kPa; elemental analysis, (calculated / found): 076.08 / 78.00, 09.33 / 9.40, 06.82 / 6.78. Example 2 The working procedure is the same as in Example 1, using 5-phenoxypentane as the alkylating agent. The product is obtained in 76% yield, m.p. 140-143 ° C / 0.05 kPa, elution analysis (calculated / found X): 077.68 / 77.76, 010.19 / 10.23, 05.66 / 5.58. Example 3 The working procedure is the same as in Example 1 as the alkylating agent and used 1-bromo-8-phenoxyoctane. The product is formed in 78 X; t.v. 165 ° C / 0.04 kPa; elemental analysis (calculated / found X): 078.84 / 78.96, 010.79 / 10.74, 04.84 / 4.80. OBJECT OF THE EXPLOSION 1. K- (ω-phenoxyalkyl) piperidines of the formula O - - Q where n denotes 2 to 10. 2. Spdsob přípravy zlúčenín podlá bodu 1, vyznačujúci sa tým, že sa nechá zreagovaťpiperidin s l-bróm-ú)-fenoxyalkánom obecného vzorca2. A process for the preparation of the compounds according to claim 1, wherein the piperidine is reacted with the 1-bromo-β-phenoxyalkane of the formula: kde n značí 2 až 10, počas 6 hodin v prostředí vriaceho benzénu*where n is 2 to 10, for 6 hours in a boiling benzene environment *
CS36279A 1979-01-17 1979-01-17 N-/omega-phenoxyalkyl/piperidines and process for preparing them CS200147B1 (en)

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