CS269563B1 - 3-cycloalkoxymethyl-4-hydroxyphenylalkylketones and method of their production - Google Patents
3-cycloalkoxymethyl-4-hydroxyphenylalkylketones and method of their production Download PDFInfo
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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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- Czechoslovakia
- Prior art keywords
- formula
- cycloalkoxymethyl
- carbon atoms
- ketones
- alkyl
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- 238000000034 method Methods 0.000 title claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 150000002576 ketones Chemical class 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- -1 3-Cyclopentoxy-4-hydroxyphenylethylketones Chemical class 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract description 3
- 239000013543 active substance Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- JEYCHXPRVCFCAQ-UHFFFAOYSA-N OC1=C(C=C(C=C1)CC(=O)CC1=CC(=C(C=C1)O)CCl)CCl Chemical compound OC1=C(C=C(C=C1)CC(=O)CC1=CC(=C(C=C1)O)CCl)CCl JEYCHXPRVCFCAQ-UHFFFAOYSA-N 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RARSHUDCJQSEFJ-UHFFFAOYSA-N p-Hydroxypropiophenone Chemical compound CCC(=O)C1=CC=C(O)C=C1 RARSHUDCJQSEFJ-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 present invention relates to novel 3-cycloalkoxymethyl-4-hydroxyphenylalkyl ketones of of formula I wherein R 1 is alkyl s . 2 With 1 to 2 carbon atoms and R is cycloalkyl with 5 to 6 carbon atoms and methods by the reaction of the corresponding 4-hydroxy-3-chloromethylphenylalkyl ketones II with relevant alcohol III in bicarbonate sodium at 30-50 ° C. Compounds of this type can be used as starting materials raw materials for biological preparation active substances.
Description
CS 269563 B1 1CS 269563 B1 1
Vynález sa týká 3-cykloalkoxymetyl^*~ftydroxymetylalkylketónov všeobecného vzorca IThe present invention relates to 3-cycloalkoxymethyl-4-hydroxy-methyl-alkyl ketones of formula (I)
OH CH20R2 COR1 1 '2 kde R je alkyl s 1 až 2 atomami uhllka, R je cykloalkyl s 5 až 6 atomami uhlíka. Látky všeobecného vzorca I sú deriváty p-hydroxyacetofenónu resp. p-hydroxypropio-fenónu, ktoré sa využívajú při přípravě látok s biologickými vlastnosfami (pri přípravě,beta-adrenolytík, antiarytmik, lokálnych anestetik) 3-cykloalkoxymetyl-4-hydroxyfenylalkylketóny všeobecného vzorca I je možné podlávynálezu připravit tak, že sa nechajú příslušné 3-chlórmetyl-4-hydroxyfenylalkylketónyvšeobecného vzorca II, připravené podlá literatury Travé R., Gazz. Chim. Ital. 01,773/1951/., Sohda S., Masatashi F., Tomazo T.,. Norujasu H., 3. Hed. Chem 22, 279 /1979/Wherein R is alkyl of 1 to 2 carbon atoms, R is cycloalkyl of 5 to 6 carbon atoms. The compounds of formula (I) are derivatives of β-hydroxyacetophenone, respectively. The p-hydroxypropionphenone used in the preparation of substances with biological properties (in the preparation, beta-adrenolytics, antiarrhythmic agents, local anesthetics) of the 3-cycloalkoxymethyl-4-hydroxyphenylalkyl ketones of the formula I can be prepared by leaving the corresponding 3 chloromethyl-4-hydroxyphenylalkyl ketones of general formula II, prepared according to the literature of Travé R., Gazz. Chim. Italian. 01,773 (1951), Sohda, S., Masatashi, F., Tomazo, T.,. Norujasu H., 3. Hed. Chem 22, 279 (1979)
. OH fm' C"2C1 í COR1. OH fm " C "
kde R1 znamená alkyl s 1 až 2 atomami uhlíka., reagovat s příslušným alkoholom všeobec-ného vzorca IIIwherein R 1 is C 1 -C 2 alkyl, reacting with the appropriate alcohol of formula III
R2 - 0 -Η III O , kde R znamená cykloalkyl s 5 až 6 atomami uhllka za přítomnosti NaHCO-j pri teplote 30 -50 °C.R 2 -O-III O, wherein R is C 5 -C 6 cycloalkyl in the presence of NaHCO 3 at 30-50 ° C.
Bližšie podrobnosti vyplynu s nasledovného spůsobu přípravy Příklad 3-cyklohexyloxy-4-hydroxyfenylmetylketon 0,14 mol 4-hydroxy-3-chlórmetylfenylmetylketón sa za laboratórnej teploty rozpustív 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 od-filtrovaní NaHCOj a oddestilování cyklohexanolu za zníženého tlaku sa olejovitý zvyšokkrystalizuje z heptánu resp. hexánu. 3-cyklohexyloxy-4-hydroxyfenylmetylketón-biela krystalická látka vzniká vo výtažku 60teorie, t.t. 61-3°C /hexán/For more details, please refer to the following procedure. Example 3-Cyclohexyloxy-4-hydroxyphenylmethylketone 0.14 mol 4-Hydroxy-3-chloromethylphenylmethyl ketone is dissolved in 150 ml cyclohexanol at room temperature and 0.29 mol NaHCO 3 is added sequentially. The mixture is reacted at room temperature for 4 hours and then heated at 30-50 ° C for 4 hours. After filtering off the NaHCO3 and distilling off the cyclohexanol under reduced pressure, the oily residue crystallized from heptane and heptane respectively. hexane. The 3-cyclohexyloxy-4-hydroxyphenylmethylketone-white crystalline solid is formed in 60% yield, m.p. 61-3 ° C / hexane /
Analýza vypočít./zistené ’ι C 72,55 / 72,77 ·-. H 8,12 / 8,05 IČ / cm”1 / V, /C=0/ 1676.,3 S > ^OC1590·’ c../ as Ar ai 1258 1h-NMR / ef" ppm/ ArCH20 4,80 /2H,s/. ., CH-jCO 2,50 /3H,s/ O-CH<" 3,45 /lH,m/., cyklohexyl 1,5-2,00 /10 H,m/Analysis calculated / found C 72.55 / 72.77 · -. H 8.12 (8.05 IR / cm @ -1), [.alpha.] D @ 20/1676. 80 (2H, s), CH 2 CO 2,50 / 3H, s / O-CH < = 3.45 (1H, m), cyclohexyl 1.5-2.00 / 10H, m / s;
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS878486A CS269563B1 (en) | 1987-11-25 | 1987-11-25 | 3-cycloalkoxymethyl-4-hydroxyphenylalkylketones and method of their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS878486A CS269563B1 (en) | 1987-11-25 | 1987-11-25 | 3-cycloalkoxymethyl-4-hydroxyphenylalkylketones and method of their production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS848687A1 CS848687A1 (en) | 1989-09-12 |
| CS269563B1 true CS269563B1 (en) | 1990-04-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS878486A CS269563B1 (en) | 1987-11-25 | 1987-11-25 | 3-cycloalkoxymethyl-4-hydroxyphenylalkylketones and method of their production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS269563B1 (en) |
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1987
- 1987-11-25 CS CS878486A patent/CS269563B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS848687A1 (en) | 1989-09-12 |
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