SU302329A1 - METHOD OF OBTAINING N-SUBSTITUTED i AMINOACETHYLADAMANTANI;;:.:? UenAi ^ v-i ^ V-iO '' ^ ^ ;; ^ ^? '' 4 - Google Patents
METHOD OF OBTAINING N-SUBSTITUTED i AMINOACETHYLADAMANTANI;;:.:? UenAi ^ v-i ^ V-iO '' ^ ^ ;; ^ ^? '' 4Info
- Publication number
- SU302329A1 SU302329A1 SU1378117A SU1378117A SU302329A1 SU 302329 A1 SU302329 A1 SU 302329A1 SU 1378117 A SU1378117 A SU 1378117A SU 1378117 A SU1378117 A SU 1378117A SU 302329 A1 SU302329 A1 SU 302329A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- substituted
- obtaining
- uenai
- aminoacethyladamantani
- nhr
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- -1 cyclohexyl- Chemical group 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 210000001736 Capillaries Anatomy 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- MFSIEROJJKUHBQ-UHFFFAOYSA-N O.[Cl] Chemical class O.[Cl] MFSIEROJJKUHBQ-UHFFFAOYSA-N 0.000 description 1
- MWFBNPVTFPRUHI-UHFFFAOYSA-N adamantane;urea Chemical class NC(N)=O.C1C(C2)CC3CC1CC2C3 MWFBNPVTFPRUHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000840 anti-viral Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 229940113083 morpholine Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к способу получени ранее не известных соединений из р да адамантана, обладающих противовирусным и психодепрессорными свойствами. Эти вещества могут найти применение и в других отрасл х фармацевтической химии.This invention relates to a process for the preparation of previously unknown compounds from the adamantane range, which possess antiviral and psychodepressant properties. These substances can be used in other fields of pharmaceutical chemistry.
Предлагаетс способ получени нового класса производных адамантана-Ы-замещенных аминоацетиладамантанов (аминокетонов адамантана) общей формулыA method is proposed for producing a new class of adamantane-L-substituted amino-acetyladomantanes (adamantane amino ketones) of the general formula
C-CH2-NHR-HC1 ОC-CH2-NHR-HC1 O
где RСНз; -СгНз; -СН(СНз)2;where RCHN; -SgNz; -CH (CH3) 2;
-С(СНз)з; циклогексил-; 1-адамантил-; -фенил; NHR-пиперидино-; морфолино-.-C (CH3) s; cyclohexyl-; 1-adamantyl; -phenyl; NHR-piperidino; morpholino.
Соединени указанной формулы предлагаетс получать из 1-бромацетиладамантана при взаимодействии его с алифатическими (нормальными и азо-алкил), алициклическими , ароматическими или гетероциклическимиCompounds of this formula are proposed to be prepared from 1-bromoacetylademutane by reacting it with aliphatic (normal and azo-alkyl), alicyclic, aromatic or heterocyclic
первичными или вторичными аминами в присутствии третичного амина (например, триэтиламина ) при нагревании до кипени в сухом бензоле с выделением целевых продуктов известными приемами, например в виде хлор гидратов.primary or secondary amines in the presence of a tertiary amine (for example, triethylamine) when heated to boiling in dry benzene and the desired products are isolated using known techniques, for example, in the form of chlorine hydrates.
Пример. 3 г 1-бромацегиладамантана раствор ют в 15 мл сухого бензола, добавл ют к раствору 1,68 мл триэтиламина и 1 мл морфолина (все компоненты реакции в мол рных соотношени х). Реакционную смесь нагревают на вод ной бане 3 час. После охлаждени отфильтровывают образовавщуюс соль триэтиламина и отгон ют бензол. Полученный амин в виде желтого масла раствор ют в сухом эфире и раствор насыщают сухим хлористым водородом. Получают 2,72 г (78%) хлоргидрата морфолиноацётиладамантана с т. пл. 250-252°С после перекристаллизации из ацетонитрила (с разложением в запа нном капилл ре).Example. 3 g of 1-bromoacetyladeanthane is dissolved in 15 ml of dry benzene, 1.68 ml of triethylamine and 1 ml of morpholine are added to the solution (all reaction components in molar ratios). The reaction mixture is heated in a water bath for 3 hours. After cooling, the triethylamine salt formed is filtered off and the benzene is distilled off. The resulting amine as a yellow oil is dissolved in dry ether and the solution is saturated with dry hydrogen chloride. Obtain 2.72 g (78%) of morpholino-acetyladamantane hydrochloride with mp. 250-252 ° С after recrystallization from acetonitrile (with decomposition in a sealed capillary).
Найдено, %: С 63,66 Н 8,50; N4,63; СП 1,76. CigHjoNOCl.Found,%: C 63.66 H 8.50; N4.63; SP 1.76. CigHjoNOCl.
Вычислено, %: С 64,10; Н 8,73; N 4,67; С1 11,82.Calculated,%: C 64,10; H 8.73; N 4.67; C1 11.82.
Аналогично получают соединени указанного типа, приведенные в таблице. Структура подтверждена анализом веществ на С, Н,. N, С1 к ИК-спектрами.Similarly, compounds of the specified type are given in the table. The structure is confirmed by the analysis of substances for С, Н ,. N, C1 to IR spectra.
Предмет изобретени Subject invention
Способ получени N-замещенных аминоацетиладамантанов общей формулыThe method of obtaining N-substituted aminoacetylamine of the General formula
С-СНг-NHFi C-SNg-NHFi
НС1 ОHC1 O
где R - -СНз; -С2Н5; where R is - SNS; -C2H5;
-СзН7; -СН(СНз)2; -С(СНз)з; циклогексил-; 1-адамантил-; феНИЛ-; NHR-пиперидино-; морфолино-, например морфолиноацетиладамантана, отличающийс тем, что 1-бромацетиладамантан обрабатывают алифатическими, алициклическими, ароматическими или гетероциклическими первичными или вторичными аминами при кип чении в сухом бензоле в присутствии третичного амина с выделением целевых продуктов известными приемами, например в виде хлоргидратов .-SzN7; -CH (CH3) 2; -C (CH3) s; cyclohexyl-; 1-adamantyl; phenyl-; NHR-piperidino; morpholino, e.g. morpholinoacetylademantane, characterized in that 1-bromoacetyladamantane is treated with aliphatic, alicyclic, aromatic or heterocyclic primary or secondary amines by boiling in dry benzene in the presence of a tertiary amine, with the release of the target products by means of known methods, for example, in the form of chlorides.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU302329A1 true SU302329A1 (en) |
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