CS200147B1

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

Info

Publication number: CS200147B1
Application number: CS36279A
Authority: CS
Inventors: Ivan Lacko; Ferdinand Devinsky; Ludovit Krasnec
Original assignee: Ivan Lacko; Ferdinand Devinsky; Ludovit Krasnec
Priority date: 1979-01-17
Filing date: 1979-01-17
Publication date: 1980-08-29

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.

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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

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

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. 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:

where n is 2 to 10, for 6 hours in a boiling benzene environment *