CS269563B1 - 3-cycloalkoxymethyl-4-hydroxyphenylalkyl ketones; - Google Patents

3-cycloalkoxymethyl-4-hydroxyphenylalkyl ketones; Download PDF

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CS269563B1
CS269563B1 CS878486A CS848687A CS269563B1 CS 269563 B1 CS269563 B1 CS 269563B1 CS 878486 A CS878486 A CS 878486A CS 848687 A CS848687 A CS 848687A CS 269563 B1 CS269563 B1 CS 269563B1
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cycloalkoxymethyl
ketones
general formula
carbon atoms
preparation
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CS878486A
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Czech (cs)
Slovak (sk)
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CS848687A1 (en
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Ruzena Rndr Csc Cizmarikova
Jozef Doc Rndr Csc Cizmarik
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Ruzena Rndr Csc Cizmarikova
Cizmarik Jozef
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Abstract

Riešenie sa týká nových 3-cykloalkoxymety1-4-hydroxyfenylalkylketónov všeobecného vzorca I, v ktorom R1 znamená alkyl s . 2 1 až 2 atomami uhlíka a R znamená cykloalkyl s 5 až 6 atómami uhlíka i spósoby pripravy reakciou příslušných 4-hydroxy3-chlórmetylfenylalkylketónov II s příslušným alkoholom III v prostředí hydrogénuhličitanu sodného pri teplote 30 až 50 °C. Zlúčeniny tohto typu sa móžu použit ako východiskové suroviny pre přípravu biologických aktívnych látok.The solution relates to new 3-cycloalkoxymethyl-4-hydroxyphenylalkyl ketones of the general formula I, in which R1 represents alkyl with . 2 1 to 2 carbon atoms and R represents cycloalkyl with 5 to 6 carbon atoms, as well as methods of preparation by reacting the corresponding 4-hydroxy3-chloromethylphenylalkyl ketones II with the corresponding alcohol III in a sodium bicarbonate environment at a temperature of 30 to 50 ° C. Compounds of this type can be used as starting materials for the preparation of biologically active substances.

Description

Vynález sa týká 3-cykloalkoxymetyl-*-hydroxymetylalkylketónov všeobecného vzorca I tmThe invention relates to 3-cycloalkoxymethyl-*-hydroxymethylalkyl ketones of the general formula I tm

'2 kde R je alkyl s 1 až 2 atómami uhlíka, R je cykloalkyl s 5 až 6 atómami uhlíka.'2 where R is alkyl having 1 to 2 carbon atoms, R is cycloalkyl having 5 to 6 carbon atoms.

Látky všeobecného vzorca I sú deriváty p-hydroxyacetofenónu resp. p-hydroxypropiofenónu, ktoré sa využívajú při přípravě látok s biologickými vlastnosťami (pri přípravě, beta-adrenolytík, antiarytmik, lokálnych anestetik)Substances of general formula I are derivatives of p-hydroxyacetophenone or p-hydroxypropiophenone, which are used in the preparation of substances with biological properties (in the preparation of beta-adrenolytic agents, antiarrhythmics, local anesthetics)

3-cykloalkoxymetyl-4-hydroxyfenylalkylketóny všeobecného vzorca I je možné podía vynálezu připravit tak, že sa nechajú příslušné 3-chlórmetyl-4-hydroxyfenylalkylketóny všeobecného vzorca II, připravené podía literatury Trave R., Gazz. Chim. Ital. 01,773 /1951/., Sohda S., Masatashi F., Tomazo T.,. Norujasu H., 3. Med. Chem 22, 279 /1979/3-Cycloalkoxymethyl-4-hydroxyphenylalkyl ketones of the general formula I can be prepared according to the invention by allowing the corresponding 3-chloromethyl-4-hydroxyphenylalkyl ketones of the general formula II, prepared according to the literature Trave R., Gazz. Chim. Ital. 01,773 /1951/., Sohda S., Masatashi F., Tomazo T.,. Norujasu H., 3. Med. Chem 22, 279 /1979/

kde R1 znamená alkyl s 1 až 2 atómami uhlíka., reagovat s příslušným alkoholom všeobecného vzorca IIIwhere R 1 means alkyl with 1 to 2 carbon atoms., to react with the corresponding alcohol of general formula III

R2 - 0 -Η IIIR 2 - 0 -Η III

O , kde R znamená cykloalkyl s 5 až 6 atómami uhlíka za přítomnosti NaHCO^ pri teplote 30 50 °C.O , where R means cycloalkyl with 5 to 6 carbon atoms in the presence of NaHCO^ at a temperature of 30 50 °C.

Bližšie podrobnosti vyplynu s nasledovného spůsobu přípravyFurther details will emerge from the following method of preparation

PříkladExample

3-cyklohexyloxy-4-hydroxyfenylmetylketon3-Cyclohexyloxy-4-hydroxyphenylmethyl ketone

0,14 mol 4-hydroxy-3-chlórmetylfenylmetylketón sa za laboratórnej teploty rozpustí v 150 ml cyklohexanolu a postupné sa přidává 0,29 mol NaHCOj. Zmes sa nechá reagovat’ 4 hodiny pri laboratórnej teplote a potom sa zahrieva 4 hodinu pri teplote 30-50°C. Po odfiltrovaní NaHCOj a oddestilování cyklohexanolu za zníženého tlaku sa olejovitý zvyšok kryštalizuje z heptánu resp. hexánu.0.14 mol of 4-hydroxy-3-chloromethylphenylmethylketone is dissolved in 150 ml of cyclohexanol at laboratory temperature and 0.29 mol of NaHCO 3 is gradually added. The mixture is left to react for 4 hours at room temperature and then heated for 4 hours at a temperature of 30-50°C. After filtering off NaHCO 3 and distilling off cyclohexanol under reduced pressure, the oily residue is crystallized from heptane or hexane.

3-cyklohexyloxy-4-hydroxyfenylmetylketón-biela krystalická látka vzniká vo výtažku 60 i teorie, t.t. 61-3°C /hexán/3-cyclohexyloxy-4-hydroxyphenylmethylketone-white crystalline substance is formed in an extract of 60 i theory, m.p. 61-3°C /hexane/

Analýza vypočít./zistené ’t C 72,55 / 72,77 % H 8,12 / 8,05Analysis calc./found ’t C 72.55 / 72.77 % H 8.12 / 8.05

IČ / cm'1 / ias/C=0/ 1676., <c=c1590., ^as/CAr° CA1/ 1250IČ / cm' 1 / i as /C=0/ 1676., < c=c 1590., ^ as /C Ar ° C A1 / 1250

Ih-NMR / d ppm/ ArCH20 4,00 /2H,s/., CHjCO 2,50 /3H,s/1h-NMR / d ppm/ ArCH 2 0 4.00 /2H,s/., CHjCO 2.50 /3H,s/

O-CH< 3,45 /lH,m/., cyklohexyl 1,5-2,00 /10 H,m/O-CH< 3.45 /1H,m/., cyclohexyl 1.5-2.00 /10 H,m/

CS:269563 Bl.CS : 269563 Bl.

S použitím uvedenej' metody bolii pní pravené’ 'naisledovné doteraz nepop í sáné: látky i >.. >Using the above-mentioned method, the following not yet described substances were prepared: substances i >.. >

1. 3-cyklopentoxy-4-hydroxy f enylmetylkeitóru; > < <t. t. 6B-71°C /heptán/1. 3-cyclopentoxy-4-hydroxy phenylmethylketor; > < <t. m.p. 6B-71°C /heptane/

2. 3-cyklopentoxy-4-hydroxyfenyletylketony t.t. 68-9°C, /heptán/2. 3-cyclopentoxy-4-hydroxyphenylethyl ketones m.p. 68-9°C, /heptane/

3. 3-cyklchexyloxy-4-hydroxyfenylmetylketón , t.t. 61-4°0 /hexán/3. 3-cyclohexyloxy-4-hydroxyphenylmethyl ketone, m.p. 61-4°0 /hexane/

4. 3-cyklohexyloxy-4-hydroxyfenyletylketón, t.t. 54-7°C /hexán/4. 3-cyclohexyloxy-4-hydroxyphenylethyl ketone, m.p. 54-7°C /hexane/

Claims (2)

PREDMET VY NÁ LEZUOBJECT OF THE FINDING 1. 3-cykloalkoxymetyl-4-hydroxyfenylalkylketóny všeobecného vzorca I OH1. 3-Cycloalkoxymethyl-4-hydroxyphenylalkylketones of general formula I OH Γ0Ρ CH20R2 Γ0Ρ CH 2 0R 2 I COR1 1 '2 · kde R je alkyl s 1 až 2 atomami uhlíka a R je cykloalkyl s 5 až atomami uhlíkaI COR 1 1 '2 · where R is alkyl with 1 to 2 carbon atoms and R is cycloalkyl with 5 to 5 carbon atoms 2. Spůsob přípravy 3-cykloalkoxymetyl-4-hydroxyfenylalkylketónov všeobecného vzorca I podlá bodu 1, vyznačujúci sa tým, že sa nechájú reagovat 4-hydroxy-3-chlórmetylfenylalkylketony všeobecného vzorca II2. Method for the preparation of 3-cycloalkoxymethyl-4-hydroxyphenylalkylketones of the general formula I according to point 1, characterized in that 4-hydroxy-3-chloromethylphenylalkylketones of the general formula II are allowed to react kde R znamená to isté ako vo vzorci I, s příslušným alkoholom všeobecného vzorca IIIwhere R means the same as in formula I, with the corresponding alcohol of general formula III R2 - 0 - H .R 2 - 0 - H . kde R2 znamená to isté ako vo vzorci I, za přítomnosti NaHCOj při teplote 30 - 50 °C.where R 2 means the same as in formula I, in the presence of NaHCO 3 at a temperature of 30 - 50 °C.
CS878486A 1987-11-25 1987-11-25 3-cycloalkoxymethyl-4-hydroxyphenylalkyl ketones; CS269563B1 (en)

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