SU374814A1 - WAY OF OBTAINING 1Ch2-CYANPHENOXY) -2-OXY-; 3-ETHYL- - Google Patents
WAY OF OBTAINING 1Ch2-CYANPHENOXY) -2-OXY-; 3-ETHYL-Info
- Publication number
- SU374814A1 SU374814A1 SU1677651A SU1677651A SU374814A1 SU 374814 A1 SU374814 A1 SU 374814A1 SU 1677651 A SU1677651 A SU 1677651A SU 1677651 A SU1677651 A SU 1677651A SU 374814 A1 SU374814 A1 SU 374814A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ethyl
- obtaining
- cyanphenoxy
- oxy
- way
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- UCYJVNBJCIZMTJ-UHFFFAOYSA-N 1-(ethylamino)propan-2-ol Chemical compound CCNCC(C)O UCYJVNBJCIZMTJ-UHFFFAOYSA-N 0.000 description 1
- -1 2-cyanophenoxy Chemical group 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N Benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-N Bromoacetic acid Chemical class OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- DFJAVDXYHCJASO-UHFFFAOYSA-N Cl.C(#N)C1=C(OCC(CNCC)O)C=CC=C1 Chemical compound Cl.C(#N)C1=C(OCC(CNCC)O)C=CC=C1 DFJAVDXYHCJASO-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N Ethyl radical Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N Propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Description
1one
Изобретение относитс к способу получени нового производного аминопропана, «оторое обладает физиологической активностью.The invention relates to a process for the preparation of a novel aminopropane derivative, which "possesses physiological activity.
Способ получени этого соединени основан на реакции алкилировани первичных аминов до получени соответствующих вторичных аминов. Однако по 1предлагаемому способу с использованием этой реакции получено новое соединение, которое обладает цен1ньгаи свойствами и может найти применение в .медицинской практике.The process for producing this compound is based on the reaction of alkylation of primary amines to the corresponding secondary amines. However, according to the proposed method, using this reaction, a new compound was obtained, which possesses price properties and can be used in medical practice.
Предла1гаетс получать 1-(2нциаНфенокси)2-окСИ-З-этиламинопропан формулыIt is proposed to obtain 1- (2N-3Nphenoxy) 2-hydroxy-3-ethylaminopropane of the formula
CN ; 0(:H2-CH(OH -CH2-NHC H5CN; 0 (: H2 — CH (OH —CH2 — NHC H5
алкилирова ием амина формулыalkyl by amine of formula
CN - OCH CHOH-CHi-NHiCN - OCH CHOH-CHi-NHi
соединением формулы CaHsX, где X - легко отщепл ема группа, например атом галогеиа , алкил или арилсульфонилаксил.a compound of the formula CaHsX, where X is an easily cleavable group, for example, a halogen atom, alkyl or arylsulfonyloxy.
Полученное по лредлагаемому способу соединение имеет асимметрический атом углерода в группировке-СНОН и поэтому может иметь форму рацемата или олтически активных антиподов . Оотически активные соединени можно получить, исход из оптически активных исходных продуктов, или расщеплением полученного рацемата с помощью обычных методик , например с использованием дибензоилвинной или бромкамфарной кислот.The compound obtained by the method described above has an asymmetric carbon atom in the -CHOH group and can therefore be in the form of a racemate or an anti-active antipode. Ootically active compounds can be prepared from optically active starting materials or by cleavage of the resulting racemate using conventional techniques, for example, using dibenzoyl tartaric or bromoacetic acids.
Полученные соединени можно переводить известным способом в соли обра-бопкой сол ной , серной, бромистоводородной, малеиновой, молочной и другими кислотами.The resulting compounds can be converted in a known manner into salts by treatment of hydrochloric, sulfuric, hydrobromic, maleic, lactic and other acids.
Пример. 1-(2-цианфенокси) - 2 - окси-3этиламинопропан-гидрохлорид . 1,14 г (0,005 моль) хлоргидрата 1-(2-цианфенокси)-2-0Кси3-аминопро1пана раствор ют в 2 НоО и прибавл ют 1,06 г (0,01 моль) соды. ПослеExample. 1- (2-cyanophenoxy) -2-hydroxy-3ethylaminopropane hydrochloride. 1.14 g (0.005 mol) of 1- (2-cyanophenoxy) -2-0Xi3-aminopropane hydrochloride is dissolved in 2 Ho and soda is added to 1.06 g (0.01 mol). After
прибавлени 12 мл этанола и 1,08 г (0,01 моль) этилбромида нагревают при размешивании до кипени с обратным холодильником. После кип чени в течение 1 час реакционную смесь концентрируют в вакууме и остаток хроматографируют на колонне с сили1ка.гелем, примен смесь из 70 этилацетата, 30 ч. изопропанола и 10 Ч. аммиака. Очищенное основание осаждаетс в этаноле как хлоргидрат и плавитс при 134-135,5° С.adding 12 ml of ethanol and 1.08 g (0.01 mol) of ethyl bromide is heated under stirring to reflux. After boiling for 1 hour, the reaction mixture was concentrated in vacuo and the residue was chromatographed on a silica gel column using a mixture of 70 ethyl acetate, 30 parts of isopropanol and 10 parts of ammonia. The purified base precipitates in ethanol as hydrochloride and melts at 134-135.5 ° C.
Предмет изобретен.и The subject of the invention.
Способ получени 1-(2-циаН|фенокси)-2-окси3-этиламино1П р1пана общей формулыThe method of obtaining 1- (2-ciaH | phenoxy) -2-hydroxy-3-ethylamino 1 p pane of the general formula
ОМOM
(ОН)-CH2-NHC2,H5(OH) -CH2-NHC2, H5
или его солей, отличающийс тем, что ъ аминопрапаи формулыor its salts, characterized in that b aminoprappai formula
OCH2CHOH-CH7-NHOCH2CHOH-CH7-NH
ввод т этильный радицал реакцией обменного разложени с соединением формулы СаНвХ, в которой X - легко отщепл емый радикал, например атом галагена, с последующим выделением целевого продукта известным способом в свободном .виде или в виде соли, в ращемической или оптиче аки активной форме.an ethyl radical is introduced by an exchange decomposition reaction with a compound of the formula CaHBX, in which X is an easily cleavable radical, such as a halagen atom, followed by isolation of the target product by a known method in a free form or optically active form.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1940566A DE1940566C3 (en) | 1969-08-08 | 1969-08-08 | 1- (2-Nitrilophenoxy) -2-hydroxy-3ethylaminopropane, process for its preparation and pharmaceuticals containing it |
| SU1469623A SU347996A1 (en) | 1970-07-30 | METHOD FOR OBTAINING OPTICAL |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SU374814A1 true SU374814A1 (en) | |
| SU374814A3 SU374814A3 (en) | 1973-03-20 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3551493A (en) | Alkyl-and cycloalkyl-amino-propanol-cyclopentyl- and cyclopentenyl-phenol ethers | |
| JPH03503163A (en) | New amines, their uses and manufacturing methods | |
| US20050032837A1 (en) | 4-Phenyl-piperidine compounds and their use as modulators of opioid receptors | |
| US5936091A (en) | Processes and intermediates for resolving piperidyl acetamide stereoisomers | |
| US7459560B2 (en) | Processes and intermediates for resolving piperidyl acetamide stereoisomers | |
| DK143128B (en) | ANALOGY PROCESSING & TASTING FOR PREPARATION OF 1-ARYLOXY-2-HYDROXY-3-ALKYLAMINOPROPANES OR THEIR PHYSIALLY ACCEPTABLE ACID ADDITION SALTS | |
| IE42119B1 (en) | Aralkylamine derivatives | |
| JP4156799B2 (en) | Phenylaminoalkylcarboxylic acid derivative and pharmaceutical composition containing the same | |
| NO178858B (en) | Analogous Process for Preparing Substituted 4-Phenyl-4-Piperidinecarboxamides with Both Local Anesthetic and Analgesic Effect | |
| US5965734A (en) | Processes and intermediates for preparing 2-substituted piperidine stereoisomers | |
| JPS595577B2 (en) | Chikansaretail Sankanshiki Amino Alcohol Seihou | |
| SU374814A1 (en) | WAY OF OBTAINING 1Ch2-CYANPHENOXY) -2-OXY-; 3-ETHYL- | |
| SU722481A3 (en) | Method of preparing aminoketone derivatives or their salts | |
| JP2012532923A (en) | Method for producing O-desmethylvenlafaxine and intermediate used therein | |
| US2852526A (en) | Substituted pyrrolidines | |
| US4032658A (en) | Alkanolamine derivatives | |
| CN1469862A (en) | 2,2-diphenyl butanamide derivatives and medicines containing the same | |
| JP4014643B2 (en) | Aryloxypropanolamine derivative, production method thereof and use thereof | |
| US1972465A (en) | Production of nitriles | |
| US3754003A (en) | Tetramethyl pyrrolidine derivatives | |
| CA1246083A (en) | Ethanolamines | |
| EP0724577A1 (en) | Heterocyclic amines for treating ischaemic strokes | |
| US4474783A (en) | Cyclopropylmethyl piperazines, the process for preparing the same and their use in therapeutics | |
| JPS6214545B2 (en) | ||
| JP2002226450A (en) | Synthesis of new polynitrile from alicyclic vicinal primary diamine |