SU450398A3 - The method of obtaining -aryl-2-aminoalkoxystyrene - Google Patents

The method of obtaining -aryl-2-aminoalkoxystyrene

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SU450398A3
SU450398A3 SU1701190A SU1701190A SU450398A3 SU 450398 A3 SU450398 A3 SU 450398A3 SU 1701190 A SU1701190 A SU 1701190A SU 1701190 A SU1701190 A SU 1701190A SU 450398 A3 SU450398 A3 SU 450398A3
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radical
substituted
lower alkyl
general formula
cis
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Эрих Мюллер
Роланд Майер
Вилли Дидерен
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Д-Р Карл Томэ Гмбх (Фирма)
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Description

1one

Изобретение относитс  к способу получени  новых р-арил-2-аминоалкоксистиролов, обладающих фармакологической активностью и могущих найти применение в медицине в качестве фармацевтических препаратов.This invention relates to a process for the preparation of novel p-aryl-2-aminoalkoxystyrenes possessing pharmacological activity and which can be used in medicine as pharmaceutical preparations.

Получение этих соединений основано на известной реакции амина с галоидным алкилом.The preparation of these compounds is based on the known reaction of an amine with alkyl halide.

Использование этой реакции в предлагаемом способе позвол ет получить новые не описанные ранее соединени , обладающие фармакологической активностью.The use of this reaction in the proposed method allows to obtain new compounds not previously described with pharmacological activity.

По предлагаемому способу были получены новые |р-арил-2-аминоалкоксистиролы общей формулы I The proposed method was obtained new | p-aryl-2-aminoalkoxystyrene of General formula I

R.R.

6-CH-CH-lCH2)6-CH-CH-lCH2)

РтRt

ЕЧ RSECH RS

или их соли с пеорганическими и органическими кислотами. В формуле I Аг означает фениловый радикал, 1-, 3-, или 4-пиридиловый радикал, который может быть замещен низщей алкильной группой; 2-хинолиловый радикал или 2-пиразиниловый радикал, который может быть замещен низщим алкилом, пиримидиловый радикал, который может быть замещен низщим алкилом, 2-бензимидазолильный радикал, который может быть замещен атомом галогена, низщим алкилом или трифторметильной группой, 2-фурил- или 2-тиениловый радикал; 5-изоксазолиловый радикал , который может быть замещен низщим алкильным или фенильным радикалом, 5-(1,2, 4-оксадиазолил)-радикал, замещенный при необходимости пизщим алкилом,or their salts with organic or organic acids. In formula I, Ar means a phenyl radical, a 1-, 3-, or 4-pyridyl radical, which may be substituted by a lower alkyl group; A 2-quinolyl radical or a 2-pyrazinyl radical which may be substituted with a lower alkyl, a pyrimidyl radical which may be substituted with a lower alkyl, a 2-benzimidazolyl radical which may be substituted with a halogen atom, a lower alkyl or a trifluoromethyl group, a 2-furyl or 2-thienyl radical; 5-isoxazolyl radical, which may be substituted by a lower alkyl or phenyl radical, 5- (1,2, 4-oxadiazolyl) -radical, optionally substituted with lower alkyl,

Ri, Ra, R4 и RS, которые могут быть одипаковыми или различпыми, означают атом водорода или низшие алкильные радикалы, RS - атом водорода, низща  алкоксигруппа. Re и RT, которые могут быть одинаковыми или различными, означают атом водорода илиRi, Ra, R4 and RS, which may be odipak or different, means a hydrogen atom or lower alkyl radicals, RS - a hydrogen atom, a lower alkoxy group. Re and RT, which may be the same or different, mean a hydrogen atom or

низщие алкил-, алкенил-, оксиалкил-, алкоксиалкиловые или аралкиловые радикалы, причем радикалы Re и R вместе с наход щимс  между ними атомом азота могут образовать насыщенное моноциклическое гетероциклическое 5-н7-членное кольцо, которое может содержать атом кислорода и/или другой атом азота, п - число О или 1.lower alkyl, alkenyl, oxyalkyl, alkoxyalkyl or aralkyl radicals, and the Re and R radicals, together with the nitrogen atom between them, can form a saturated monocyclic heterocyclic 5-n7-membered ring which may contain an oxygen atom and / or another atom nitrogen, n is O or 1.

По предлагаемому способу новые соединени  формулы I получают путем реакции обменного разложени  соединени  общей формулы IIAccording to the proposed method, new compounds of formula I are obtained by the reaction of exchange decomposition of compounds of general formula II

0-CH-CH-toH,)n-Z ft Rs0-CH-CH-toH,) n-Z ft Rs

в которой радикалы Аг, и п имеют указанные значени  и Z означает замен емую основными радикалами группу, например атом галогена или тиозильную группу, с амином общей формулы IIIin which the radicals Ar, and p have the indicated meanings, and Z means a group replaced by basic radicals, for example a halogen atom or a thiosyl group, with an amine of the general formula III

Вб WB

Н-И EvN and ev

в которой радикалы Re и Ry имеют указанные значени .in which the radicals Re and Ry have the indicated meanings.

Реакцию провод т в растворителе в присутствии св зывающего кислоту агента. В качестве св зывающих кислоту средств используют любые неорганические или органические основани  или избыток амина формулы III; последний одновременно может служить в качестве растворител . Реакци  протекает при повышенных температурах, обычно при 60- 120°С. Если примен ют легколетучий амин формулы III, то реакцию обменного разложени  целесообразно проводить в закрытом сосуде .The reaction is carried out in a solvent in the presence of an acid binding agent. As an acid binding agent, any inorganic or organic base or an excess of amine of formula III is used; the latter can simultaneously serve as a solvent. The reaction proceeds at elevated temperatures, usually at 60-120 ° C. If a volatile amine of formula III is used, the exchange decomposition reaction is expediently carried out in a closed vessel.

Соединени  формулы I образуютс  в виде смеси цис- и гранс-изомеров.The compounds of Formula I are formed as a mixture of cis and gran isomers.

Цис- и транс-соединени  можно разделить путем фракционной кристаллизации.Cis and trans compounds can be separated by fractional crystallization.

Соединени  формулы I обычным способом можно переводить в соли с помощью неорганических или органических кислот. В качестве кислот используютс  сол на , бромистово дородна , серна , фосфорна , винна , п-толуолсульфокислота .The compounds of formula I can be converted into salts with inorganic or organic acids in a conventional manner. Salt, methyl bromide, sulfuric, phosphoric, tartaric, p-toluenesulfonic acid are used as acids.

Пример. 16 г (2-хлорэтокси)-стирол пиридина (т. пл. 57-59°С) раствор ют в 50 мл метанола и при -15°С смещивают с 120 мл свежевз того из баллона жидкого метиламина и в автоклаве в течение 4 ч нагревают до 80°С. После охлаждени  и снижени  давлени  смесь в автоклаве упаривают, остаток раствор ют в разбавленной уксусной кислоте и два раза взбалтывают с простым эфиром , чтобы удалить слабоосновные продукты. Затем при охлаждении 2 н. раствором едкого натра подщелачивают и реакционный продукт экстрагируют уксусным эфиром. После сушки над сульфатом натри  и дистилл ции образуетс  масл нистый остаток, который при сто нии в течение 5-10 ч закристаллизовываетс  (выход 13,8 г, что соответствует 88,2% от теории).Example. 16 g of (2-chloroethoxy) pyridine styrene (m.p. 57-59 ° C) is dissolved in 50 ml of methanol and shifted from 120 ml of freshly from a container of liquid methylamine and in an autoclave at -15 ° C for 4 hours heated to 80 ° C. After cooling and pressure reduction, the mixture is evaporated in an autoclave, the residue is dissolved in dilute acetic acid and shaken twice with ether to remove weakly basic products. Then when cooled 2 n. caustic soda solution is alkalinized and the reaction product is extracted with ethyl acetate. After drying over sodium sulfate and distillation, an oily residue is formed, which crystallizes on standing for 5-10 hours (yield 13.8 g, corresponding to 88.2% of theory).

Вещество раствор ют в 200 мл ацетона, фильтруют через активированный уголь и прибавл ют 20 мл этанола. К этому раствору осторожно добавл ют 15,3 мл этанольного раствора 12,72%-ной сол ной кислоты (вес/объем ) в 50 мл ацетона до по влени  желтого окращивани , дл  чего требуетс  59 мл кислого осаждающего раствора. Затем до по влени  помутнени  добавл ют простой эфир и размешивают при охлаждении на лед ной бане. В течение 1 ч выкристаллизовываетс  бледно-желтое вещество, которое отсаСывают иThe substance is dissolved in 200 ml of acetone, filtered through activated charcoal and 20 ml of ethanol is added. To this solution, 15.3 ml of ethanolic solution of 12.72% hydrochloric acid (w / v) in 50 ml of acetone are carefully added until a yellow color is obtained, which requires 59 ml of acidic precipitating solution. Ether is then added to the appearance of turbidity and stirred while cooling in an ice bath. Within 1 hour, a pale yellow substance crystallizes out, which is filtered off and

сушат в эксикаторе. Получают 9,3 г (52% отdried in a desiccator. 9.3 g are obtained (52% of

теории) 2- 2- (2-метиламилоэтокси) - стирол пиридипмоногидрохлорида ст. пл. 178-180°С.theory) 2- 2- (2-methylaminoethoxy) - styrene pyridipmonohydrochloride st. square 178-180 ° C.

По способу, описанному в примере 1 получают также следующие вещества.According to the method described in example 1, the following substances are also obtained.

Из (2-хлорэтокси) -стирил -пиридина (т. пл. 57-59°С) и аммиака получают (2аминоэтокси )-стирол - ниридиндигидрохлорид (т. пл. 269°С, выход 49% от теории).From (2-chloroethoxy) styryl-pyridine (mp. 57-59 ° C) and ammonia, (2-amino-ethoxy) -styrene — niridinedihydrochloride (mp. 269 ° C, 49% yield of theory) is obtained.

Из (2-хлорэтокси)-стирил - хинолингидрохлорида (т. пл. 214-220°С) и метиламина получают (2-метиламиноэтокси) -стирол хинолинмоногидрохлорид (т. пл. 170°С, выход 12,0% от теории).From (2-chloroethoxy) -styryl-quinoline hydrochloride (mp 214-220 ° C) and methylamine, (2-methylaminoethoxy) styrene-quinoline monohydrochloride (mp 170 ° C, yield 12.0% of theory) is obtained.

Из (2-хлорэтокси)-стирил -пиридина (т. пл. ) и этиламина получают (этиламиноэтокси) - стирол - пиридиндигидрохлорид (т. пл. 211°С, выход 48,3% от теории).From (2-chloroethoxy) -styryl-pyridine (m.p.) and ethylamine, (ethylaminoethoxy) -styrene-pyridine dihydrochloride is obtained (m.p. 211 ° C, yield 48.3% of theory).

Из (2-хлорэтокси)-стирил -пиридина (т. пл. 57-58°С) и пиперидина получают (2-пиперидиноэтокси) - стирол - пиридиндигидрохлорид (т. пл. 176°С, выход 31% от теории).From (2-chloroethoxy) -styryl-pyridine (mp. 57-58 ° C) and piperidine, (2-piperidinoethoxy) - styrene - pyridine dihydrochloride (mp. 176 ° C, 31% yield from theory) is obtained.

Из (2-хлорэтокси)-стирил -пиридина (т. пл. 57-59°С) и морфолина получают (2-морфолиноэтокси)-стирол - пиридипдигидрохлорид . т. пл. 248°С, выход 53% от теории.From (2-chloroethoxy) -styryl-pyridine (mp. 57-59 ° C) and morpholine, (2-morpholinoethoxy) -styrene — pyridipihydrochloride is obtained. m.p. 248 ° C, yield 53% of theory.

Из (2-хлорэтокси)-стирил -пиридина (т. пл. 57-58°С) и метил-2-оксиэтиламина получают (2-Ы-метил-Н-гидроксиэтиламиноэтокси )-стирол -пиридиндигидрохлорид. Т. пл. 190°С, выход 42% от теории.From (2-chloroethoxy) styryl-pyridine (mp. 57-58 ° C) and methyl 2-hydroxyethylamine, (2-N-methyl-N-hydroxyethylaminoethoxy) -styrene-pyridine dihydrochloride is obtained. T. pl. 190 ° C, yield 42% of theory.

Из (2-хлорэтокси)-стирил -пиридина (т. пл. 57-59°С) и диметиламина получают (2-диметиламиноэтокси) - стирол - пиридинмоногидрохлорид . Т. пл. 183°С, выход 68% от теории.From (2-chloroethoxy) -styryl-pyridine (mp. 57-59 ° C) and dimethylamine, (2-dimethylaminoethoxy) -styrene-pyridine monohydrochloride is obtained. T. pl. 183 ° C, yield 68% of theory.

Из (2-хлорэтокси)-стирил -хинолина (т. пл. 214-220°С) и диметиламина получают (2-диметиламиноэтокси) - стирол - хинолинмоногидрохлорид . Т. пл. 188°С, выход 74% от теории.From (2-chloroethoxy) -styryl-quinoline (mp 214-220 ° C) and dimethylamine, (2-dimethylaminoethoxy) -styrene-quinoline monohydrochloride is obtained. T. pl. 188 ° C, yield 74% of theory.

Предмет изобретени Subject invention

Claims (3)

1. Способ получени  р-арил-2-аминоалкокси65 стиролов общей формулы (I)1. Method for preparing p-aryl-2-amino-alkoxy65 styrenes of the general formula (I) 0-CH-CH-(CH,)n-N 0-CH-CH- (CH,) n-N В RSIn RS где Ar - фенил, 2-, 3- или 4-пиридиловый радикал, который может быть замещен низшим алкилом, 2-хинолиловый радикал или 2-ниразиниловый радикал, который может быть замещен низшим алкилом, пиримидиловый радикал, который может быть замещен низшим алкилом, 2-бензимидазолильный радикал , который может быть замещен атомом галогена, низщим алкилом или трифторметильной группой, 2-фурил-, 2-тиениловый радикал , 5-изоксазолиловый радикал, который может быть замещен низшим алкилом, или фенилом, 5-(1,2,4-оксадиазолил)-радикал, который может быть замещен низшим алкилом,where Ar is a phenyl, 2-, 3- or 4-pyridyl radical, which may be substituted by lower alkyl, 2-quinolyl radical or 2-nirazinyl radical, which may be substituted by lower alkyl, pyrimidyl radical, which may be substituted by lower alkyl, A 2-benzimidazolyl radical, which may be substituted by a halogen atom, a lower alkyl or trifluoromethyl group, a 2-furyl, 2-thienyl radical, a 5-isoxazolyl radical, which may be substituted by lower alkyl, or phenyl, 5- (1,2, 4-oxadiazolyl) -radical, which can be substituted by lower al kilo iRi, R2, R4, Rs - одинаковые или различные водород или алкил,iRi, R2, R4, Rs are the same or different hydrogen or alkyl, Rs - водород или алкоксигруппа.Rs is hydrogen or alkoxy. Re и R7 - одинаковые или различные водород , низший алкил-, низший алкенил-, оксиалкил- , алкоксиалкиловый или аралкиловый радикал, причем радикалы Re и R вместе с наход щимс  между ними атомом азота могут образовывать 5-н7-членное насыщенное моноциклическое гетероциклическое кольцо.Re and R7 are the same or different hydrogen, lower alkyl, lower alkenyl, hydroxyalkyl, alkoxyalkyl or aralkyl radical, and Re and R radicals together with the nitrogen atom between them can form a 5-membered saturated monocyclic heterocyclic ring. которое может еще содержать атом кислорода или другой атом азота,which may still contain an oxygen atom or another nitrogen atom, п - число О или 1,n is the number O or 1, отличающийс  тем, что соединение общей формулы IIcharacterized in that the compound of general formula II BiВ,BiB АР-С-С- .AR-C-C. ВAT о-сн-сн-(снг)п-гO-ns-ns- (cis) p-g Bi КбBi Kb где Аг, RI-RS и п имеют указанные значени , Z - группа, замен ема  основными радикалами ,Where Ar, RI-RS and p have the indicated meanings, Z is a group that is replaced by basic radicals, подвергают взаимодействию с амином общей формулы IIIsubjected to interaction with the amine of General formula III .. в-1з(1z ( ВтW где RS и Rr имеют указанные значени , с последующим выделением целевого продукта в свободном виде или в виде соли.where RS and Rr have the indicated meanings, followed by isolation of the desired product in free form or as a salt. 2.Способ по п. 1, отличающийс  тем, что процесс провод т при 60-120°С.2. A method according to claim 1, characterized in that the process is carried out at 60-120 ° C. 3.Способ по п. 1, отличающийс  тем, что смесь цис- и транс-изомеров целевого продукта раздел ют, например фракционной кристаллизацией .3. The method according to claim 1, characterized in that the mixture of cis and trans isomers of the target product is separated, for example, by fractional crystallization.
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DE2943405A1 (en) * 1979-10-26 1981-05-07 Basf Ag, 6700 Ludwigshafen NEW AMINO DERIVATIVES OF 5- (2-HYDROXYSTYRYL) -ISOXAZOLE
DE3006809A1 (en) * 1980-02-23 1981-09-24 Basf Ag, 6700 Ludwigshafen 2 - ((3-AMINO-2-HYDROXY-PROPOXY) -STYRYL) -ISOXAZOLES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING THEM
JPS5874379U (en) * 1981-11-16 1983-05-19 富士通株式会社 electronic equipment
NO174506B (en) * 1984-10-30 1994-02-07 Usv Pharma Corp Analogous procedure for the preparation of therapeutically active compounds
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