SU496722A3 - Способ получени аминов - Google Patents
Способ получени аминовInfo
- Publication number
- SU496722A3 SU496722A3 SU1839168A SU1839168A SU496722A3 SU 496722 A3 SU496722 A3 SU 496722A3 SU 1839168 A SU1839168 A SU 1839168A SU 1839168 A SU1839168 A SU 1839168A SU 496722 A3 SU496722 A3 SU 496722A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- propanol
- yloxy
- hydrochloride
- ethane
- producing amines
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 7
- 150000001412 amines Chemical class 0.000 title description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 229960004592 isopropanol Drugs 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241001543870 Yola Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- VPGZUPPYAVLUNW-UHFFFAOYSA-N boron;tribromoborane Chemical compound [B].BrB(Br)Br VPGZUPPYAVLUNW-UHFFFAOYSA-N 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/34—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/38—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/52—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
- oKcii
или ацйлоксигруппа; - водород, бензйЯ ил адкйл 1-4 атомами углеро а;
- водород, бензил- или алки :
с атомами углерода;
лв X целое число 1 или 2, обладающих ценныктк свойстБами. Согласно изобретению опйсь ваетсй ov; соб получени аминов обшей 1 или их сопей, эаключаюшкйсй Е Toivj, -JTO соединение общей 2
РЙ4
-7 ОСИ
он
где R, , R, и .имекуг укаэанньЕе
значени .;
Ял - апкил- ИНН аралкалгруппа, подвергают реакциидезтерйфнкации Е :.олученное прм этом соединение выдел ют или этерифицируют известкь :-,;:и методами. К числу Kcxonjibisi npo.ajiJTOB, приемлемых дл осущес влени реакций деэтерифи-кации , относ тс ккспоты Л&гОйеа, 1агфи мер трехбромйстьгй бор и треххлористый алюминий, хлоргидрат пиридкнв; в том слу- , когда Кл - бэнэилгру па, к.-1ожно
примен ть метод ката итического гчдриг)о-« ваки .
Целевые продукты вьщелйю известными способа ии Б Ш1де основани или , в виде рацемата или onTts :ecKS актиБко: о антипода.
П р и м в ,р 1„ 3.-;-:Зо™.Ппскш1ам но „{в -метокеи- , 4-этан- , 2 3
4-тетрагидронафт-5 и лосси) -Е-пропано п в .. виде гкдрохпорида |4,5 г)
хлорид пиридина (S г) каграваю в р о фаре азота при 180 С Е те::ение
5час. Твердую массз раобавп ют водой
{GO мп} и отдельным ; поршпчд прибавл ют бикарбонат нафи С б гК Зыделнв шийс после эт-ого тв ердьЕй продукт от- фмпьтровыванУ - и прОх -гывв.ют водой. После кристаллизации из этилацетата nojrjrtrasoT 1 иэопропиламтда-3 (8-оксп -1, 4-этанfit 2,,3, 4-тетрагидрокафт-Б«-нлоксн)
-2-.пропанол {3,8 г, т. .,л, 134 135°С). Гилрохлорнд может г/мть голучен путем растворени свободного основани в ;о:ета.ноле , насыщенного газообразным хлористым водородог-,1, раобавленйем ДКЭТИЛОВЬЕМ , отфильтровываннем твердого осадКа н кристаллизациай из .90%-ного изопропаиола .
При осушествлении описанного метода лг; i :;v . -трэт -бутилаfvHHO-S-{8-окси- , 4 , 2, 3, 4-тетрагидроаефг 5.илокси)-2 Пропанол {т. пл. 1В1 .152°С) и его гидрохлорид (т. пл. 235237 С) и 1-втор,-бутиламин: сжси .1 4™этан-1, 2, 3, 4-.теТ;,.:- ..г афт „5 -илокси )2-пропанол и егс гидре хлорид Ст4 ЯЛ, гпшроллоридр 1 ЯВ-190 0).
Г о :й L-л ер 2, 1 - гзо-Пропила «шно ,.3„.С8-бензк;юксг ™1 4;.этан-1, 2, 3, 4---тэтраг щрона : ; -З -илоксИ;-2- Пропаноп liO г), рйствсрэнкый в 3GO мл смеси, cocTosFiiefl --,э В9%. этанола и хлористого метп -зг;а; f л ; П , гидрируют под давЛЕНпем 4..-5 атм в присугствик 3 г iD паллади ка yvrs. По окончании поглощэиШ ьсдород;,;:, через 1 час (2 мол ) сме фпльт-уют. «т.:л«ва:Ют досуха и полученньп твердый fTp3,r-. кристаллизуют из пропане в ЦЛЯ ;ТОЛ;; Г Е-: КЯ ГЯЯрОХЛОрйДа 1 КЗОПрО- .,,, -.-,,„ о SO,.,.,- у oinii 1 о
и,:-;,,.;: -.i.l.J--..:...,1,л--л- , г -сЗ 1 ii I .™ J, , ri , tJ ,
-L т.:o ;Зйгкдроиафт--5 --илокси)™2 пропацол
(7.У, li, т. пл„ 198 .ЯОО°С):
.1
П р S :3 3, Гп,ДрОХЛОрКД- l K3Onpi1;; ,: .ifiv-HiHo. 3- (8Мбтокси6епзокоDборнаи-5 - ;7к;ч .,.;:;,оп иола (5 г), растворенньж Е у.:л юфО11Ьле мл), обрабатывают ц.чн . :зх5пом)«;тъ1м бором (10 г), rac bOt- вьпеп г;;; .пот Б течение 2 час при 0(Г, Bb:;i-;- ;::K;Gj посу з и остаток pacTi.: psijoT Б 5%--иой с- 1-:;ОЧ кислоте. Смесь rjov-ioBaioT прч температуре кипени с об;:з1Яьил холо;:иль- р5коы 3 теченив 24 чаС; пе - бтткарбонатом натри и экстргируют этилаце -атом (две порции по 200 выпрг шанк досуха остаток o6pfi6aTbiFia OT раствором хлористого водород ,: 5 изопролйьоле. После разбавлени /лютиловым эфу:роч происходит осаждение гкд/э:1Ор Г, Л -тзопрог-члами о-З™{8« онпнбензо и;рЬоркан-5 :Локси|-.2-проп нО па {т. г:л. 178..-...).
При ссущег-тЕлении описенного метода получаго-г .;-5утилал- ино..-3(8-окси«. бакзонор6орг ал -5-илокси )2 -пропанол : глде гидпохлорнда (т, пл. 1Э ™193°С) и .:)з гиламиио-«3 -f 8 окскбензокорб&г:а Ь-нлокси )--.про;1л;-ол В виде гидре™
И р и ;л ер 4. Гилро ларид 1--изотл;|3-, пила ГИо- 3--(8-ацеток л---1 4 -этан-1л Я , 3, 4 -летраглдронафТ 5 Илокси).. -прлиакопа (2 г) растгоркют г. метаноле
I лО мл,л IliiCbiUOHKOM ЛЛСр;СТЫМ ВОДОрО-
сил, к нагревают в те-:ение 1 часа при ех;полагупе кипени с обратнь м холодкльнутлом . 1 iocne З-паризаинй остаток кристеплв зуот из нзопропанола длс получени гидрО .хлорида 1-изопропиламино-3-(8-юкси-1, 4 этан-1, 2, 3, 4 тетрагидронафт-. -5 илокси)2 пропанола (1,6 г, т. пп, 200-201°С). Аналогично получают следующие соединени : 1-трет.-бутиламино-3-(8-окси-1, 4-9тан-1 , 2, 3, 4-тетрагидронафт-5-ило кси)-2-пропанол в виде гидрохлорида, т. пл 235-237°С; .-бутиламино-3-{8-оксв 1, 4-этан-З ., 2, 3, 4-тетрагидронафт 5илокси )-2-пропанол в виде гидрохлорида, т. пл. 188-190°С, 1-иэопропиламино-3-(8-оксибенэонорбо нан-5 илокси)-2-пропанол в виде гидрохло рида, т, пл. 178-180°С; 1-трет.-бутиламино-3(8-оксибенэонор борнан-Б-илокси)-2-пропанол; 1-вторгбутиламино 3-{8-оксибензонорборнан-5 -илокси )-2-пропанол. Пример 5. Хлорангийрид уксусной кислоты (0,98 мл) прибавл ют к 1-изопро пиламино-3-(8-окси-1,4-этан-1 2, 3, 4 тетрагидронафт 5-илокси)-2-пропа- нолу (3,1 г) в безводном хлороформе (8О мл). Смесь нагревают при температуре кипеки с o6paTEbi;v хододильником в течение 4 час, затем упаривают досуха, обрабатывают остаток водой, фильтруют и фильтра-Е нейтрализуют твердым бикарбонатом натри . Выделившеес при этом масло экстрагируют этилацетатом (три порцки по 100 мл) и экстракт лпаривают до небольшого объема, касышают газообразным лористым водородом и затем разбавл ют диэтиловым эфиром. Полученный гидрохлорид : 1-кзолро1шламнно-3- -(8-ацетокси 1,4-этан-1. 2, 3, 4-тетрагидронафт-б-илокси )-2-пропанола отфильтровывают и кристаллизуют из изопропанола; , т пл. гидрохгюрида 185-187 С редметизобретени Cnociio получени аминов обще формуОСН - СН - СН . N 1 R где R - окси- или ацилоксигруппа Я2 - водсфод, бензил или 1алкипгруппа с 1-4 атомами углерода; R - - водород, бензил- или алкил-( Труппа с ll-io атомами углерода; X - целое число 1 или 2, или их солей, тличающийс тем, что сонение общей формулы 2 СН . N 2 , Rjj и X имеют указанные ени ; R - алкил- или аралкилгруппа, одвергают реакции деэтерификации и ченное при этом соединение выдел ют этерифицируют известными методами следующим выделением целевого проа в виде основани или соли, в виде мата или оптт-ески активногО анти .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3012471 | 1971-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU496722A3 true SU496722A3 (ru) | 1975-12-25 |
Family
ID=11229158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1839168A SU496722A3 (ru) | 1971-10-21 | 1972-10-19 | Способ получени аминов |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS515379B2 (ru) |
| AT (1) | AT318563B (ru) |
| AU (1) | AU471732B2 (ru) |
| BE (1) | BE790188R (ru) |
| CA (1) | CA992983A (ru) |
| CH (1) | CH565741A5 (ru) |
| CS (1) | CS161064B2 (ru) |
| DE (1) | DE2251095C3 (ru) |
| DK (1) | DK135576B (ru) |
| FR (1) | FR2157897B2 (ru) |
| GB (1) | GB1351557A (ru) |
| HK (1) | HK9377A (ru) |
| HU (1) | HU165185B (ru) |
| IL (1) | IL40610A (ru) |
| KE (1) | KE2693A (ru) |
| MY (1) | MY7700158A (ru) |
| NL (1) | NL153516B (ru) |
| NO (1) | NO130643C (ru) |
| SE (1) | SE389103B (ru) |
| SU (1) | SU496722A3 (ru) |
| ZA (1) | ZA727459B (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1436860A (en) * | 1972-12-18 | 1976-05-26 | Syntex Inc | 5,8-dihydro-5,8-methanonaphthalene cardiovascular agents |
| JPS52120690A (en) * | 1976-04-02 | 1977-10-11 | Fujitsu Ltd | Radiation semi-conductor device |
-
0
- BE BE790188D patent/BE790188R/xx active
-
1972
- 1972-09-21 AT AT813372A patent/AT318563B/de not_active IP Right Cessation
- 1972-09-26 AU AU47077/72A patent/AU471732B2/en not_active Expired
- 1972-09-26 GB GB4447572A patent/GB1351557A/en not_active Expired
- 1972-10-09 CS CS6793A patent/CS161064B2/cs unknown
- 1972-10-11 NO NO3647/72A patent/NO130643C/no unknown
- 1972-10-18 DE DE2251095A patent/DE2251095C3/de not_active Expired
- 1972-10-18 IL IL40610A patent/IL40610A/xx unknown
- 1972-10-18 NL NL727214106A patent/NL153516B/xx unknown
- 1972-10-19 ZA ZA727459A patent/ZA727459B/xx unknown
- 1972-10-19 DK DK515372AA patent/DK135576B/da unknown
- 1972-10-19 SU SU1839168A patent/SU496722A3/ru active
- 1972-10-20 FR FR7237226A patent/FR2157897B2/fr not_active Expired
- 1972-10-20 HU HUEA113A patent/HU165185B/hu unknown
- 1972-10-20 JP JP47105138A patent/JPS515379B2/ja not_active Expired
- 1972-10-20 CH CH1539372A patent/CH565741A5/xx not_active IP Right Cessation
- 1972-10-20 SE SE7213548A patent/SE389103B/xx unknown
- 1972-10-20 CA CA154,342A patent/CA992983A/en not_active Expired
-
1977
- 1977-01-25 KE KE2693A patent/KE2693A/xx unknown
- 1977-02-17 HK HK93/77A patent/HK9377A/xx unknown
- 1977-12-30 MY MY158/77A patent/MY7700158A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1351557A (en) | 1974-05-01 |
| NL153516B (nl) | 1977-06-15 |
| JPS4849750A (ru) | 1973-07-13 |
| SE389103B (sv) | 1976-10-25 |
| DK135576C (ru) | 1977-10-31 |
| CS161064B2 (ru) | 1975-05-04 |
| NL7214106A (ru) | 1973-04-25 |
| BE790188R (fr) | 1973-04-17 |
| HK9377A (en) | 1977-02-25 |
| FR2157897B2 (ru) | 1975-06-20 |
| IL40610A0 (en) | 1972-12-29 |
| DE2251095C3 (de) | 1976-01-02 |
| ZA727459B (en) | 1974-05-29 |
| NO130643B (ru) | 1974-10-07 |
| FR2157897A2 (ru) | 1973-06-08 |
| MY7700158A (en) | 1977-12-31 |
| AU471732B2 (en) | 1976-04-29 |
| DE2251095A1 (de) | 1973-05-10 |
| AU4707772A (en) | 1974-04-04 |
| CA992983A (en) | 1976-07-13 |
| AT318563B (de) | 1974-10-25 |
| KE2693A (en) | 1977-02-11 |
| JPS515379B2 (ru) | 1976-02-19 |
| IL40610A (en) | 1975-04-25 |
| HU165185B (ru) | 1974-07-27 |
| CH565741A5 (ru) | 1975-08-29 |
| DE2251095B2 (de) | 1975-05-07 |
| NO130643C (ru) | 1975-01-15 |
| DK135576B (da) | 1977-05-23 |
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