SE429042B - SET TO MAKE PYRIDINE CARBOXYL ACID PIPERAZIDES - Google Patents
SET TO MAKE PYRIDINE CARBOXYL ACID PIPERAZIDESInfo
- Publication number
- SE429042B SE429042B SE7807383A SE7807383A SE429042B SE 429042 B SE429042 B SE 429042B SE 7807383 A SE7807383 A SE 7807383A SE 7807383 A SE7807383 A SE 7807383A SE 429042 B SE429042 B SE 429042B
- Authority
- SE
- Sweden
- Prior art keywords
- general formula
- acid
- given above
- meaning given
- piperazides
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
10 15 25 50 55 7307385-0 HN N-ïfl v där RW har ovan angiven betydelse, i en smälta vid 140-250°C under 20-25 timmar. b) ' Pyridinkarboxylsyra omvandlas till ett motsvarande es- ter- eller amidderivat, som därefter omsättes med ett pipera- zinderivat med den ovan definierade allmänna formeln V på sätt som beskrivas under a) här ovan. c) Pyridinkarboxylsyra omvandlas till en motsvarande syra- klorid, som därefter omsättes med en förening med den ovan de- finierade allmänna formeln V vid en temperatur mellan O och lOO°C. 10 15 25 50 55 7307385-0 HN N-ï fl v where RW has the meaning given above, in a melt at 140-250 ° C for 20-25 hours. b) 'Pyridinecarboxylic acid is converted to a corresponding or amide derivatives, which are then reacted with a pipera- zinder derivatives of the general formula V defined above in a manner described under a) above. c) Pyridinecarboxylic acid is converted to a corresponding acid chloride, which is then reacted with a compound having the above procedure. defined general formula V at a temperature between 0 and 100 ° C.
De ovan beskrivna metoderna a) och b) kan genomföras med ett utbyte av ca 40-60% och metoden c) ger ett utbyte av 68% av det teoretiska. Oavsett enligt vilken metod produkten framställts kan den renas genom destillatíon i vakuum.The methods a) and b) described above can be carried out with a yield of about 40-60% and the method c) gives a yield of 68% of the theoretical. Regardless of which method the product prepared, it can be purified by distillation in vacuo.
För att finna en godtagbar förklaring av de relativt låga utbytena vid metoden a) övervakades reaktionen medelst termogravimetri. Det visade sig då att när smält pyridin-2- karboxylsyra omsättes med N-bensylpiperazin eller när pyridin- 2-karboxylsyra och N-bensylpiperazin smältes tillsammans upp- trädde en väsentlig viktförlust redan vid l20°C pà grund av en dekarboxylerande bireaktion. Med andra ord beledsagas huvud- reaktionen, när den genomföras inom ett optimalt temperatur- intervall, av en bireaktion som resulterar i en avsevärd för- lust av slutprodukten.To find an acceptable explanation of the relative low yields in method a) the reaction was monitored by thermogravimetry. It was then found that when molten pyridine-2- carboxylic acid is reacted with N-benzylpiperazine or when pyridine 2-Carboxylic acid and N-benzylpiperazine were melted together. significant weight loss occurred already at 120 ° C due to a decarboxylating side reaction. In other words, the main the reaction, when carried out within an optimum temperature interval, of a side reaction that results in a significant lust of the end product.
Vid metoden b) skulle man kunna vänta sig något gynn- sammare utbyten, men om man beaktar att man för framställning av utgångsföreningarna måste tillgripa ett ytterligare reak- tionssteg, är det totala utbytet lika lågt som eller t.o.m. lägre än vid metod a). Å andra sidan har metoderna b) och c) ytterligare nack- delar i det att vid metod b) framställningen av utgàngsmateria- let och den avsevärda mängd amoniak som utvecklas under reak- tionen medför föroreningsproblem och vid metod c) är den bil- dade saltsyran mycket svår att binda och eliminera.In method b) one could expect something favorable safer exchanges, but if one considers that one for production of the starting compounds must resort to a further reaction step, the total yield is as low as or t.o.m. lower than in method a). On the other hand, methods b) and c) have additional parts of the fact that in method b) the production of starting materials and the significant amount of ammonia evolved during the reaction causes pollution problems and in method c) the car- hydrochloric acid very difficult to bind and eliminate.
Föreliggande uppfinning siktar på ett förfarande för \n 10 15 7807383-0 framställning av de föreningar som faller under den ovan de- finierade allmänna formeln I, vilket förfarande icke är be- häftat med de ovannämnda nackdelarna, dvs. låga eller måttli- ga utbyten, långa reaktíonstider, höga temperaturer, rening medelst fraktionerad destillation i vakuum och bildning av biprodukter, som förorenar omgivningen.The present invention aims at a method for \ n 10 15 7807383-0 preparation of the compounds falling within the above defined general formula I, which procedure is not attached to the above-mentioned disadvantages, i.e. low or moderate yields, long reaction times, high temperatures, purification by fractional distillation in vacuo and formation of by-products, which pollute the environment.
Det har nu helt överraskande visat sig att nästan alla de ovan uppräknade nackdelarna kan elimineras och en extremt ren slutprodukt erhållas om man omsätter ett organiskt eller oorganiskt salt av pyridinkarboxylsyra med formeln \\ l coon II / N med en klormyrsyraester med den allmänna formeln G1 - CO, - R III där R representerar en alkylgrupp med l-5 kolatomer, i ett inert lösningsmedel och därefter omsätter det så erhållna py- ridinkarboxylsyraderivatet med formeln \\ I / -ci-o-coga Iv N o där R har ovan angiven betydelse, företrädesvis utan.föregåen- de separation, med ett piperazinderivat med den ovan definiera- de allmänna formeln V, varpà man, om man så önskar, omvandlar den så erhållna föreningen I till ett syraadditionssalt därav genom omsättning med en lämplig organisk eller oorganisk syra.It has now quite surprisingly turned out that almost everyone the above listed disadvantages can be eliminated and an extreme pure end product is obtained if one sells an organic or inorganic salt of pyridinecarboxylic acid of the formula \\ l coon II / N with a chloroformic acid ester of the general formula G1 - CO, - R III where R represents an alkyl group having 1 to 5 carbon atoms, in one inert solvent and then react the pyramid thus obtained. the ridicarboxylic acid derivative of the formula \\ I / -ci-o-coga Iv N o where R has the meaning given above, preferably without separation, with a piperazine derivative having the the general formula V, whereupon, if desired, converted the compound I thus obtained into an acid addition salt thereof by reaction with a suitable organic or inorganic acid.
Som inert lösningsmedel kan användas vilket som helst lösningsmedel som icke deltar i den kemiska reaktionen under de givna betingelserna och följaktligen icke har någon inverkan på reaktionens förlopp. Tetrahydrofuran, dimetylformamid, di- metylsulfoxid, dioxan och etylacetat har visat sig vara exempel på för ändamålet användbara lösningsmedel.Any inert solvent can be used solvents which do not participate in the chemical reaction during the given conditions and consequently has no effect on the course of the reaction. Tetrahydrofuran, dimethylformamide, di- methyl sulfoxide, dioxane and ethyl acetate have been found to be examples on solvents useful for the purpose.
Det som utgångsmaterial använda saltet av pyridinkar- boxylsyra kan framställas med en tertiär amin, exempelvis 10 15 55 vsoivzas-o i 4 trietylamin eller N-metylmorfolin eller med en oorganisk bas, exempelvis kaliumhydroxid, men andra alkalimetallsalter kan också med fördel användas.The salt of the pyridine carcinogen used as starting material boxylic acid can be prepared with a tertiary amine, for example 10 15 55 vsoivzas-o i 4 triethylamine or N-methylmorpholine or with an inorganic base, for example potassium hydroxide, but other alkali metal salts can also advantageously used.
När man utgår från salter framställda med organiska baser sker reaktionen i allmänhet i ett homogent medium och en föregående saltframställning erfordras icke. Om man däre- mot framställer ett salt med en oorganisk bas sker reaktionen i ett heterogent medium och saltet måste först framställas.When starting from salts made with organic bases, the reaction generally takes place in a homogeneous medium and a prior salt preparation is not required. If you against producing a salt with an inorganic base, the reaction takes place in a heterogeneous medium and the salt must first be prepared.
Reaktionen kan genomföras inom ett brett temperatur- intervall utan att det uppträder någon nämnvärd förändring av utbytet. Temperaturen ligger i allmänhet mellan -20 och +40°C, företrädesvis mellan -5 och +20°C. _ När reaktionsblandningen behandlas med vatten utfaller dihydratet av produkten i kristallinisk form och efterföljande rening medelst fraktionerad destillation i vakuum kan uteläm- nas. 1 Huvudfördelarna med förfarandet enligt uppfinningen i jämförelse med de tidigare kända är följande: Reaktionen avslutas inom kort tid Ingen förhöjd temperatur erfordras Ingen specialutrustning erfordras Biprodukterna är icke miljöskadliga Föreningarna I kan erhållas nästan kvantitativt och med utmärkt renhet.The reaction can be carried out within a wide temperature range. intervals without any appreciable change in the yield. The temperature is generally between -20 and + 40 ° C, preferably between -5 and + 20 ° C. _ When the reaction mixture is treated with water, it precipitates the dihydrate of the product in crystalline form and subsequently purification by fractional distillation in vacuo can be omitted nas. 1 The main advantages of the process according to the invention in comparison with the previously known are the following: The reaction is terminated shortly No elevated temperature is required No special equipment required The by-products are not harmful to the environment The compounds I can be obtained almost quantitatively and with excellent purity.
Uppfinningen belyses i närmare detalj i följande icke begränsande exempel.The invention is not further elucidated in the following restrictive examples.
Exem el 1: Framställnin av l-bens 1-4- 2'- ikol l - i erazin. 246,2 g (2,0 mol) pyridin-2-karboxylsyra omsattes med 202,4 g (2,0 mol) trietylamin i etylacetat, varpå reaktionsblandningen vid en temperatur mellan -5 och 0°C försattes med 217,1 g (2 mol) etylklorformiat och omrördes vid nämnda temperatur i 50 minuter. Därefter behandlades reaktionsblandningen med 552,5 g (2,0 mol) N-bensylpiperazin i 400 ml etylacetat i en halv tim- me. När tíllsatsen av denna lösning slutförts ommördes reak- tionsblandningen i ytterligare två timmar vid lO°C. Etylace- tatlösningen industades i vakuum, varpå återstoden 1östes*i metanol och utfälldes med vatten. Utbyte 615 g (97%). Det mot- svarande dihydratets smältpunkt var 81-82°C. xn 10 IU \.Y1 u: (D \N \,*1 7807383-0 \;'1 Analys %C %H 95N Beräknat för Cl?H35N50.2 H20 64,55 7,50 15,24 Funnet 64,25 7,42 15,15 Det motsvarande vätefumaratets smältpunkt var 165-l66°C (i litteraturen angiven smältpunkt l64°C).Example 1: Preparation of 1-benz 1-4-2'-carbon 1 - in erazine. 246.2 g (2.0 mol) of pyridine-2-carboxylic acid were reacted with 202.4 g (2.0 mol) of triethylamine in ethyl acetate, then the reaction mixture at a temperature between -5 and 0 ° C was added 217.1 g (2 mol) of ethyl chloroformate and stirred at said temperature for 50 minutes. Then the reaction mixture was treated with 552.5 g (2.0 mol) of N-benzylpiperazine in 400 ml of ethyl acetate for half an hour me. When the addition of this solution was completed, the reaction the mixture for a further two hours at 10 ° C. Ethyl- the tat solution was evaporated in vacuo and the residue was dissolved in methanol and precipitated with water. Yield 615 g (97%). The opposite the melting point of the corresponding dihydrate was 81-82 ° C. xn 10 IU \ .Y1 u: (D \ N \, * 1 7807383-0 \; '1 Analysis% C% H 95N Calculated for Cl? H35N50.2 H20 64.55 7.50 15.24 Found 64.25 7.42 15.15 The melting point of the corresponding hydrogen fumarate was 165-166 ° C (melting point l64 ° C given in the literature).
Exempel 2: Framställning av l-metyl-4-(5'-nikotinoyl)-pipera- 35:13. 16,1 g; (0,l mol) kaliumsalt av nikotinsyra omsattes med 10,8 5 (0,1 mol) etylklorformiat i en blandning av dimetyl- formamid och tetrahydrofuran vid en temperatur mellan -5 och O°C och reaktionsblandningen försattes vid samma temperatur med 10,0 g (0,1 mol) metylpiperazin löst i etylacetat. Bland- ningen omrördes vid +l0°C i ytterligare två timmar och in- dunstades därefter i vakuum. Återstoden löstes i dikloretan och den erhållna lösningen tvättades med vatten, indunstades och återstoden fraktionerades i vakuum. Utbyte 18,25 g (89,0%).Example 2: Preparation of 1-methyl-4- (5'-nicotinoyl) -pipera- 35:13. 16.1 g; (0.1 mol) of potassium salt of nicotinic acid was reacted with 10.8 (0.1 mol) of ethyl chloroformate in a mixture of dimethyl- formamide and tetrahydrofuran at a temperature between -5 and 0 ° C and the reaction mixture was added at the same temperature with 10.0 g (0.1 mol) of methylpiperazine dissolved in ethyl acetate. Among- The mixture was stirred at + 10 ° C for a further two hours and then evaporated in vacuo. The residue was dissolved in dichloroethane and the resulting solution was washed with water, evaporated and the residue was fractionated in vacuo. Yield 18.25 g (89.0%).
Kokpunkt 146-l49°G/0,1 mmHg.Boiling point 146-149 ° G / 0.1 mmHg.
Analys %C %H %N ßerälmat för Cllfllâivöo 64, 56 7,5 20 A7 Funnet 64,15 7,45 20,56 Det motsvarande diklorhydratets smältpunkt 150%.Analysis% C% H% N ßerälmat for Cll fl lâivöo 64, 56 7.5 20 A7 Found 64.15 7.45 20.56 Melting point 150% of the corresponding dichlorohydrate.
Exempel 5: Framställning av 1-metyl-4-(4'-isonikotinoyl)- Qioerazín. l2,š g (0,1 mol) isonikotinsyra omvandlades till ett salt genom omsättning med 10,1 g (0,1 mol) N-metylmorfolin i etylacetatlösning vid rumstemperaturen, varpå reaktionsbland- ningen försattes med 9,40 g (0,1 mol) metylklorformiat vid en temperatur mellan -5 och O°C och därefter med 10,0 g (0,1 mol) N-metylpiperazin i etylacetat vid samma temperatur. När tillsatsen slutförts omrördes reaktíonsblandningen i två tim- mar vid +l0°C. Den erhållna N-metylmorfolin-hydrokloriden av- Filtrcrades, filtratet indunstades och återstoden fraktionera- des i vakuum. Utbyte 17,2 g (8w%). Kokpunkt 147-149°C/0,2 mmHg.Example 5: Preparation of 1-methyl-4- (4'-isonicotinoyl) - Qioerazín. 1.2 g (0.1 mol) of isonicotinic acid were converted to a salt by reaction with 10.1 g (0.1 mol) of N-methylmorpholine in ethyl acetate solution at room temperature, whereupon The mixture was added with 9.40 g (0.1 mol) of methyl chloroformate at a temperature between -5 and 0 ° C and then with 10.0 g (0.1 mol) N-methylpiperazine in ethyl acetate at the same temperature. When After the addition was complete, the reaction mixture was stirred for two hours. mar at + 10 ° C. The resulting N-methylmorpholine hydrochloride Filtered, the filtrate evaporated and the residue fractionated. des in vacuum. Yield 17.2 g (8w%). Boiling point 147-149 ° C / 0.2 mmHg.
Analys %C %H %N Beräknat för CllH15N5O 64,56 7,57 20,47 Funnet 64,52 7,48 20,31 Det motsvarande diklorhydratets smältpunkt 27l°C.Analysis% C% H% N Calculated for C 11 H 15 N 5 O 64.56 7.57 20.47 Found 64.52 7.48 20.31 Melting point 271 ° C of the corresponding dichlorohydrate.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU77EE2510A HU175075B (en) | 1977-06-30 | 1977-06-30 | Process for preparing pyridine-carboxylic acid piperazides |
Publications (2)
Publication Number | Publication Date |
---|---|
SE7807383L SE7807383L (en) | 1978-12-31 |
SE429042B true SE429042B (en) | 1983-08-08 |
Family
ID=10995734
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7807383A SE429042B (en) | 1977-06-30 | 1978-06-29 | SET TO MAKE PYRIDINE CARBOXYL ACID PIPERAZIDES |
Country Status (15)
Country | Link |
---|---|
JP (1) | JPS5414985A (en) |
AT (1) | AT365172B (en) |
CA (1) | CA1103252A (en) |
CH (1) | CH634572A5 (en) |
CS (1) | CS199212B2 (en) |
DD (1) | DD136136A5 (en) |
DE (1) | DE2828888A1 (en) |
DK (1) | DK148771C (en) |
FI (1) | FI66174C (en) |
GB (1) | GB2001062B (en) |
HU (1) | HU175075B (en) |
PL (1) | PL110336B1 (en) |
SE (1) | SE429042B (en) |
SU (1) | SU715023A3 (en) |
YU (1) | YU40711B (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3985066A (en) * | 1975-05-15 | 1976-10-12 | S&S Corrugated Paper Machinery Co., Inc. | Single point means for slotter adjustment |
DE10035908A1 (en) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | New heteroaryl derivatives and their use as medicines |
US6953801B2 (en) | 2001-05-22 | 2005-10-11 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted 1-benzyl-4-aryl piperazine analogues |
NZ598891A (en) * | 2009-08-24 | 2014-05-30 | Neuralstem Inc | Synthesis of a neurostimulative piperazine |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3865828A (en) * | 1972-03-22 | 1975-02-11 | Egyt Gyogyszervegyeszeti Gyar | Pyridine derivatives having antidepressant activity |
GB1451994A (en) * | 1973-07-20 | 1976-10-06 | Smithe Machine Co Inc F L | Method and apparatus for cutting and applying patches |
JPS5144957A (en) * | 1974-10-14 | 1976-04-16 | Matsushita Electric Works Ltd | DEJITARU TOKEI |
JPS5246080A (en) * | 1975-10-06 | 1977-04-12 | Taiho Yakuhin Kogyo Kk | Preparation of pyridinecarbonyl aminoalkyl thiols |
-
1977
- 1977-06-30 HU HU77EE2510A patent/HU175075B/en not_active IP Right Cessation
-
1978
- 1978-06-20 CA CA305,894A patent/CA1103252A/en not_active Expired
- 1978-06-21 AT AT0453178A patent/AT365172B/en active
- 1978-06-26 SU SU782628948A patent/SU715023A3/en active
- 1978-06-26 FI FI782031A patent/FI66174C/en not_active IP Right Cessation
- 1978-06-26 DK DK285178A patent/DK148771C/en not_active IP Right Cessation
- 1978-06-26 YU YU1499/78A patent/YU40711B/en unknown
- 1978-06-28 DD DD78206341A patent/DD136136A5/en not_active IP Right Cessation
- 1978-06-28 GB GB7828118A patent/GB2001062B/en not_active Expired
- 1978-06-29 JP JP7918978A patent/JPS5414985A/en active Granted
- 1978-06-29 PL PL1978208009A patent/PL110336B1/en unknown
- 1978-06-29 CS CS784300A patent/CS199212B2/en unknown
- 1978-06-29 SE SE7807383A patent/SE429042B/en not_active IP Right Cessation
- 1978-06-29 CH CH709078A patent/CH634572A5/en not_active IP Right Cessation
- 1978-06-30 DE DE19782828888 patent/DE2828888A1/en active Granted
Also Published As
Publication number | Publication date |
---|---|
PL110336B1 (en) | 1980-07-31 |
JPS5414985A (en) | 1979-02-03 |
CS199212B2 (en) | 1980-07-31 |
GB2001062B (en) | 1982-02-24 |
CA1103252A (en) | 1981-06-16 |
DD136136A5 (en) | 1979-06-20 |
DE2828888C2 (en) | 1987-10-29 |
JPS6152826B2 (en) | 1986-11-14 |
YU149978A (en) | 1982-10-31 |
SE7807383L (en) | 1978-12-31 |
HU175075B (en) | 1980-05-28 |
DK148771C (en) | 1986-03-10 |
FI782031A (en) | 1978-12-31 |
FI66174B (en) | 1984-05-31 |
GB2001062A (en) | 1979-01-24 |
SU715023A3 (en) | 1980-02-05 |
DE2828888A1 (en) | 1979-01-18 |
FI66174C (en) | 1984-09-10 |
DK285178A (en) | 1978-12-31 |
CH634572A5 (en) | 1983-02-15 |
ATA453178A (en) | 1981-05-15 |
AT365172B (en) | 1981-12-28 |
YU40711B (en) | 1986-04-30 |
DK148771B (en) | 1985-09-23 |
PL208009A1 (en) | 1979-05-07 |
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