CS236149B1 - Method of n-(1,3-diphenyl-2-propyl)piperazine derivatives preparation and of its dihydrochloride - Google Patents
Method of n-(1,3-diphenyl-2-propyl)piperazine derivatives preparation and of its dihydrochloride Download PDFInfo
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- CS236149B1 CS236149B1 CS641183A CS641183A CS236149B1 CS 236149 B1 CS236149 B1 CS 236149B1 CS 641183 A CS641183 A CS 641183A CS 641183 A CS641183 A CS 641183A CS 236149 B1 CS236149 B1 CS 236149B1
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- Czechoslovakia
- Prior art keywords
- propyl
- dihydrochloride
- dimethoxyphenyl
- phenyl
- formula
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- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims abstract description 6
- 150000004885 piperazines Chemical class 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 18
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 3
- 239000011541 reaction mixture Substances 0.000 claims abstract description 3
- 238000006467 substitution reaction Methods 0.000 claims abstract description 3
- LQYGPQBBALGYDA-UHFFFAOYSA-N 4-(2-chloro-3-phenylpropyl)-1,2-dimethoxybenzene Chemical compound C1=C(OC)C(OC)=CC=C1CC(Cl)CC1=CC=CC=C1 LQYGPQBBALGYDA-UHFFFAOYSA-N 0.000 claims description 5
- KWZHBNYIZRGJAZ-UHFFFAOYSA-N 1-(1,3-diphenylpropan-2-yl)piperazine Chemical class C=1C=CC=CC=1CC(N1CCNCC1)CC1=CC=CC=C1 KWZHBNYIZRGJAZ-UHFFFAOYSA-N 0.000 claims description 2
- -1 1- [1-Phenyl-3- (3,4-dimethoxyphenyl) -2-propyl] -4-methylpiperazine Chemical compound 0.000 abstract description 5
- 238000009835 boiling Methods 0.000 abstract description 2
- 239000002327 cardiovascular agent Substances 0.000 abstract description 2
- 229940125692 cardiovascular agent Drugs 0.000 abstract description 2
- 125000005805 dimethoxy phenyl group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 description 1
- VKASSGAQVBXUQF-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-phenylpropan-2-one Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)CC1=CC=CC=C1 VKASSGAQVBXUQF-UHFFFAOYSA-N 0.000 description 1
- ASLSUMISAQDOOB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1OC ASLSUMISAQDOOB-UHFFFAOYSA-N 0.000 description 1
- DXOOZNXXECBXSO-UHFFFAOYSA-N COC=1C=C(C=CC1OC)C(C#N)C(CC1=CC=CC=C1)=O Chemical compound COC=1C=C(C=CC1OC)C(C#N)C(CC1=CC=CC=C1)=O DXOOZNXXECBXSO-UHFFFAOYSA-N 0.000 description 1
- JGQIWJXGXMCSLS-UHFFFAOYSA-N COC=1C=C(C=CC1OC)C(C(=O)N)C(CC1=CC=CC=C1)=O Chemical compound COC=1C=C(C=CC1OC)C(C(=O)N)C(CC1=CC=CC=C1)=O JGQIWJXGXMCSLS-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000000508 neurotrophic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001304 sample melting Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Vynález spadá do oboru synthetických léčiv. Jeho předmětem je způsob přípravy 1-/1-Íeny1-3-(3, 4—dimethoxyfenyl)-2-propyl/-4n»thylpiperazinu vzorce I a jeho dihydrochloridu. Látka vzorce I je meziproduktem přípravy neurotropně. psychotropně a kardiovaskulárně účinných léčiv. Způsob přípravy podle vynálezu spočívá v substituční reakci 1-feny1-3-(3,4- dimethoxyfenyl)-2-propylchloridu s přebytečným l-methylpiperazinem při teplotách od 100 °C do teploty varu reakční směsi a v následující neutralizaci získané báze I chlorovodíkem nebo kyselinou chlorovodíkovou.The invention is within the scope of synthetic drugs. His subject is a method of preparation 1- [1-Phenyl-3- (3,4-dimethoxyphenyl) -2-propyl] -4-methylpiperazine of Formula I and its dihydrochloride. Formula I is intermediate preparation neurotrophically. psychotropically and cardiovascular drugs. The process of the invention is based on the invention in the 1-phenyl-1-3- substitution reaction (3,4- of dimethoxyphenyl) -2-propyl chloride with excess 1-methylpiperazine at temperatures from 100 ° C to the boiling point of the reaction mixture and in subsequent neutralization of the base obtained With hydrochloric acid or hydrochloric acid.
Description
Vynález se týká způsobu přípravy N-(1,3-difenyl-2-propyl)piperazinového derivátu vzorce IThe invention relates to a process for the preparation of an N- (1,3-diphenyl-2-propyl) piperazine derivative of the formula I
OkC) (i)OkC) (i)
N VUCtta jeho dihydrochloridu.N VUCtta of its dihydrochloride.
Látka vzorce I je meziproduktem přípravy neurotropních, psychotropních a kardiovaskulárních léčiv a jako taková je technicky důležitá·The compound of formula I is an intermediate in the preparation of neurotrophic, psychotropic and cardiovascular drugs and as such is technically important ·
Způsob přípravy látky I podle tohoto vynálezu spočívá v substituční reakci 1-fenyl-3-(3,4-diraethoxyfenyl)-2-propylchloridu vzorce II <XI) ακρ' clThe process for the preparation of the compound (I) according to the invention consists in the substitution reaction of 1-phenyl-3- (3,4-diethoxyphenyl) -2-propyl chloride of the formula II ( XI).
I z s 1-methylpiperazinem. Tato reakce se provádí s výhodou za použití přebytku 1-methylpiperazinu, připadne za přítomnosti dimethylformamidu a jodidu draselného při teplotách od 100 °C do teploty varu reakční směsi· Přebytečný 1-methylpiperazin působí nejen jako reaktant, ale také jako činidlo odnímající chlorovodík reakcí vzniklý. Reakcí se získá olejovitá ba?ae vzorce I, která se neutralisací chlorovodíkem nebo kyselinou chlorovodíkovou převede na krystalický dihydrochlorid, který poskytuje vyhovující analysu a v čistém stavu taje při 171 až 174 °C. Výchozí 1-fenyl-3-(3,4-dimethoxyfenyl)-2-propylchlorid je látkou novou, jejíž příprava je popsána v dále uvedeném příkladu. Tento příklad má za účel ilustrovat jednu z možností1 with 1-methylpiperazine. This reaction is preferably carried out using an excess of 1-methylpiperazine, optionally in the presence of dimethylformamide and potassium iodide at temperatures from 100 ° C to the boiling point of the reaction mixture. The reaction yields an oily ba ? and (e) which is converted to crystalline dihydrochloride by neutralization with hydrochloric acid or hydrochloric acid, which gives a satisfactory analysis and melts at 171-174 ° C in the pure state. The starting 1-phenyl-3- (3,4-dimethoxyphenyl) -2-propyl chloride is a novel compound, the preparation of which is described in the example below. This example is intended to illustrate one possibility
236 149 vynálezu se všemi podrobnostmi, avšak není jeho účelem vyčerpávajícím způsobem všechny možnosti vynálezu popisovat.236,149 of the invention in full detail, but is not intended to be exhaustive.
Směs 87 g 1-feny1-3-(3,4-dimethoxyfenyl)-2-propy1chloridu, 6,0 g jodidu draselného, 60 ml dimethylformamidu a 100 gA mixture of 87 g of 1-phenyl-3- (3,4-dimethoxyphenyl) -2-propyl chloride, 6.0 g of potassium iodide, 60 ml of dimethylformamide and 100 g.
1- methylpiperazinu se míchá a zahřívá pod zpětným chladičem h na 125 až 130 °C, Potom se těkavé komponenty směsi odpaří ve vakuu z lázně vyhřáté až na 100 °C, zbytek se rozpustí v 500 ml toluenu a roztok se několikrát promyje vodou. Zásaditý produkt se potom převede do vodné fáze třepáním s. přebytečnou 5M-HC1 (provede se třikrát). Spojené kyselé vodné roztoky se zfiltrují s aktivním uhlím, filtrát se zalkaliauje 20% roztokem hydroxidu sodného a báae se extrahuje toluenem. Extrakt se vysuší uhličitanem draselným a odpaří. Získá se 8,0 g olejovité base I, Rozpustí se v ethanolu a přidá se slabý přebytek roztoku chlorovodíku v etheru. Stáním vykrystaluje 8,0 g dihydrochloridu látky I, tj. 1-/1-fenyl-3-(3,4-dimethoxyfenyl)2- propyl/-4-methylpiperazinu,The 1-methylpiperazine is stirred and refluxed at 125-130 ° C. The volatile components of the mixture are then evaporated under vacuum from a bath heated to 100 ° C, the residue is dissolved in 500 ml of toluene and the solution is washed several times with water. The basic product is then transferred to the aqueous phase by shaking with excess 5M-HCl (performed three times). The combined acidic aqueous solutions were filtered with charcoal, the filtrate basified with 20% sodium hydroxide solution and extracted with toluene. The extract was dried over potassium carbonate and evaporated. 8.0 g of oily base I are obtained. It is dissolved in ethanol and a slight excess of a solution of hydrogen chloride in ether is added. On standing, 8.0 g of the dihydrochloride of compound I, i.e. 1- (1-phenyl-3- (3,4-dimethoxyphenyl) 2-propyl) -4-methylpiperazine, crystallized,
Výchozí 1-fenyl-3-(3,4-dimethoxyfenyl)-2-propylchlorid je látkou novou, kterou lze připravit např. dále uvedeným postupem ze známých a komerčně přístupných surovin sThe starting 1-phenyl-3- (3,4-dimethoxyphenyl) -2-propyl chloride is a novel substance which can be prepared, for example, from known and commercially available raw materials as follows.
Ve 150 ml ethanolu se rozpustí 9,2 g sodíku, k vzniklému roztoku ethoxidu sodného se přidá 35,4 g 3,4-dimethoxyfenylacetonitrilu a potom 40,0 g fenyloctanu ethylnatého. Získaná směs se míchá a vaří pod zpětným chladičem po dobu 3,5 h, ponechá se přes noc při teplotě místnosti v klidu a potom se vlije do 600 g směsi ledu a vody. Míchá se 15 min a promyje se etherem. Vodná alkalická vrstva, obsahující sodnou sůl enolu, se oddělí a okyselí 75 ml 5M-HC1. Uvolněný 2-(3,4-dimethoxyfenyl)-3-oxo-4-fenylbutyronitrii se isoluje extrakcí etherem, extrakt se vysuší síranem sodným a odpaří, Olejovitý zbytek (60 g) je uvedený surový nitril, který se rozpustí v 600 ml kyseliny octové, k roztoku se přidá 400 ml kyseliny chlorovodíkové a směs se zahřeje na 35 až 50 °C« Potom se ponechá 48 h v klidu při teplotě místnosti. Vlije se do 6 1 vody při 10 °C, míchá se 30 min, vyloučený produkt se odsaje, promyje vodou a vysuší. Získá se 40,4 g (64 %) 2-(3,4-dimethoxyfenyl)3- oxo-4-fenylbutyramidu tajícího při 137 až 143 °C. Analytický9.2 g of sodium are dissolved in 150 ml of ethanol, and 35.4 g of 3,4-dimethoxyphenylacetonitrile is added to the resulting sodium ethoxide solution, followed by 40.0 g of ethyl phenylacetate. The resulting mixture was stirred and refluxed for 3.5 h, allowed to stand overnight at room temperature and then poured into 600 g of ice / water. Stir 15 min and wash with ether. The aqueous alkaline layer containing the enol sodium salt was separated and acidified with 75 mL of 5M-HCl. The liberated 2- (3,4-dimethoxyphenyl) -3-oxo-4-phenylbutyronitrile is isolated by ether extraction, the extract is dried over sodium sulphate and evaporated. 400 ml of hydrochloric acid are added to the solution, and the mixture is heated to 35-50 ° C. It is poured into 6 L of water at 10 ° C, stirred for 30 min, the precipitated product is filtered off with suction, washed with water and dried. 40.4 g (64%) of 2- (3,4-dimethoxyphenyl) -3-oxo-4-phenylbutyramide, melting at 137-143 ° C, is obtained. Analytic
236 149 vzorek se získá rekrystalisací z ethanolu, t.t. 158 až 159 °C.236 149 sample was obtained by recrystallization from ethanol, m.p. Mp 158-159 ° C.
Suspenze 15,7 g předešlého amidu v 550 ml 10% kyseliny chlorovodíkové se míchá a vaří 6 h pod zpětným chladičem. Po ochlazení se směs extrahuje etherem, extrakt se promyje 10% roztokem hydrogenuhlicitanu sodného a vodou, vysuší se chloridem vápenatým a odpaří. Zbytek se rozpustí v 35 ml ethanolu, .roztok se zfiltruje s aktivním uhlím a filtrát se odpaří ve vakuu. Zbytek krystaluje stáním přes noc. Získá se 10,8 g (80 %) 1-feny1-3-(3>4-dimethoxyfenyl)propan-2-onu tajícího při 32 až 35 °C. Krystalizaci ze směsi benzenu a petroletheru se získá analytický Vzorek tající při 38 až 41 °C.A suspension of 15.7 g of the above amide in 550 ml of 10% hydrochloric acid was stirred and refluxed for 6 hours. After cooling, the mixture was extracted with ether, the extract was washed with 10% sodium bicarbonate solution and water, dried over calcium chloride and evaporated. The residue is dissolved in 35 ml of ethanol, the solution is filtered with charcoal and the filtrate is evaporated in vacuo. The residue crystallizes on standing overnight. 10.8 g (80%) of 1-phenyl-3- (3,4-dimethoxyphenyl) propan-2-one melting at 32-35 ° C is obtained. Crystallization from benzene / petroleum ether gave an analytical sample melting at 38-41 ° C.
K míchané směsi 15,0 g předešlého ketonu s 2-20 ml ethanolu se zvolna přidá 10,0 g natriumborohydridu. Směs se potom vaří 5 h pod zpětným chladičem, po ochlazení se rozloží přídavkem 50 ml vody a ethanol se oddestiluje. Zbytek se zředí 150 ml vody, okyselí se 100 ml 2,5M-HC1 a extrahuje benzenem. Extrakt se vysuší.síranem hořečnatým a odpaří. Získá se 15,3 g (100 %3 surového olejovitého 1-feny1-3-(3,4-dimethoxyfenyl)propan-2-olu. Pro analytické účely se vzorek předestiluje} t.v. 142 °C/30 Pa.To a stirred mixture of 15.0 g of the previous ketone with 2-20 mL of ethanol was slowly added 10.0 g of sodium borohydride. The mixture is then refluxed for 5 hours, quenched by the addition of 50 ml of water and the ethanol is distilled off. The residue was diluted with 150 mL of water, acidified with 100 mL of 2.5 M HCl and extracted with benzene. The extract was dried over magnesium sulphate and evaporated. 15.3 g (100% 3 of crude oily 1-phenyl-3- (3,4-dimethoxyphenyl) propan-2-ol) are obtained and the sample is distilled for b.p.
K roztoku 115 g předešlého surového chloridu v 500 ml benzenu se za míchání zvolna přikape roztok 95 g thionylchloridu ve 100 ml benzenu a směs se vaří 1,5 h pod zpětným chladičem. Po odpaření těkavých podílů za sníženého tlaku se získá homogenní odparek ve výtěžku 108 g (89 %), který představuje žádaný 1-feny1-3-(3,4-dimethoxyfenyl)-2-propylchlorid.To a solution of 115 g of the previous crude chloride in 500 ml of benzene, a solution of 95 g of thionyl chloride in 100 ml of benzene is slowly added dropwise with stirring, and the mixture is refluxed for 1.5 hours. After evaporation of the volatiles under reduced pressure, a homogeneous residue is obtained in a yield of 108 g (89%) which is the desired 1-phenyl-3- (3,4-dimethoxyphenyl) -2-propyl chloride.
Pro analytické účely se. vzorek předestiluje ve vakuuj t.v.For analytical purposes:. the sample distilled under vacuum.
154 až 156 °C/30 Pa.154-156 ° C / 30 Pa.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS641183A CS236149B1 (en) | 1983-09-02 | 1983-09-02 | Method of n-(1,3-diphenyl-2-propyl)piperazine derivatives preparation and of its dihydrochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS641183A CS236149B1 (en) | 1983-09-02 | 1983-09-02 | Method of n-(1,3-diphenyl-2-propyl)piperazine derivatives preparation and of its dihydrochloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS236149B1 true CS236149B1 (en) | 1985-05-15 |
Family
ID=5411084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS641183A CS236149B1 (en) | 1983-09-02 | 1983-09-02 | Method of n-(1,3-diphenyl-2-propyl)piperazine derivatives preparation and of its dihydrochloride |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS236149B1 (en) |
-
1983
- 1983-09-02 CS CS641183A patent/CS236149B1/en unknown
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