FI59587C - NYTT FOERFARANDE FOER FRAMSTAELLNING AV PIPERAZINDERIVAT - Google Patents
NYTT FOERFARANDE FOER FRAMSTAELLNING AV PIPERAZINDERIVAT Download PDFInfo
- Publication number
- FI59587C FI59587C FI793712A FI793712A FI59587C FI 59587 C FI59587 C FI 59587C FI 793712 A FI793712 A FI 793712A FI 793712 A FI793712 A FI 793712A FI 59587 C FI59587 C FI 59587C
- Authority
- FI
- Finland
- Prior art keywords
- piperazinderivat
- foerfarande foer
- foer framstaellning
- nytt foerfarande
- h3co
- Prior art date
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
r,, .... KUULUTUSJULKAISU ¢-0507 VST* M <11> utlKogninosskrift 5»00 / C (45) Patentti myönnetty 10 09 1931 .tfiÄjöj Patent rceddelat v v y (51) Kv.ik.Wci.3 c 07 D 295/16 SUOMI —FINLAND (M) htM«MiMM-PmnMieknlii| 793712 (22) KUkcmtapilvI—AiN&knlngadaf 27.11.79 (Fl) (23) AlkupUv·—Glltlfhattdtf 15.06.72 (41) Tullut JulklMkil—Uhrit 0#T*mH| 27.11.79r ,, .... ADVERTISEMENT ¢ -0507 VST * M <11> utlKogninosskrift 5 »00 / C (45) Patent granted 10 09 1931 .tfiÄjöj Patent rceddelat vvy (51) Kv.ik.Wci.3 c 07 D 295 / 16 FINLAND —FINLAND (M) htM «MiMM-PmnMieknlii | 793712 (22) KUkcmtapilvI — AiN & knlngadaf 27.11.79 (Fl) (23) AlkupUv · —Glltlfhattdtf 15.06.72 (41) Tullut JulklMkil — Uhrit 0 # T * mH | 11/27/79
Htwtttl- ja r^imrlWIItu. 0„Htwtttl- and r ^ imrlWIItu. 0 "
Pmtant- och mlUtritynlun AnaMan utfafd od) utl-*k«1ft*n publicurad 29.05.Oi (32)(33)(31) «tty ueiollwu·—toflrt prioritat (71) Delalande S.A., 32 rue Henri Regnault, Courbevoie (Hauts-de-Seine),Pmtant- och mlUtritynlun AnaMan utfafd od) utl- * k «1ft * n publicurad 29.05.Oi (32) (33) (31)« tty ueiollwu · —toflrt priority (71) Delalande SA, 32 rue Henri Regnault, Courbevoie (Hauts -de-Seine),
Ranska-Frankrike(FR) (72) Gerard Huguet, Le Pinson Malesherbes (Loiret), Claude Fauran, Paris,France-France (FR) (72) Gerard Huguet, Le Pinson Malesherbes (Loiret), Claude Fauran, Paris,
Guy Raynaud, Paris, Bernard Pourrias, Meudon La Foret (Hauts-de-Seine), Michel Turin, Paris, Ranska-Frankrike(FR) (7*0 Leitzinger Oy (5*0 Uusi menetelmä piperatsiinijohdannaisen valmistamiseksi - Nytt förfarande för framställning av piperazinderivat (62) Jakamalla erotettu hakemuksesta 1712/72 - Avdelad frän ansökan 1712/72 Tämän keksinnön kohteena on uusi menetelmä kaavan I mukaisen yhdisteen valmistamiseksiGuy Raynaud, Paris, Bernard Pourrias, Meudon La Foret (Hauts-de-Seine), Michel Turin, Paris, France-France (FR) (7 * 0 Leitzinger Oy (5 * 0 New method for the preparation of a piperazine derivative) The present invention relates to a new process for the preparation of a compound of formula I.
H3COH3CO
h3co —CH = CH “ C0 " _/NH U> H3C0h3co —CH = CH "C0" _ / NH U> H3CO
Keksinnön mukaan valmistetut kaavan I mukaiset yhdisteet ovat käyttökelpoisia valmistettaessa farmaseuttisesti arvokkaita piperatsiinijohdannaisia, joiden kaava onThe compounds of formula I prepared according to the invention are useful in the preparation of pharmaceutically valuable piperazine derivatives of formula
H3COH3CO
H3C0 -0 CH = CH - CO - ^ - CH2 - CO R (II>H3CO-O CH = CH - CO - ^ - CH2 - CO R (II>
H3COH3CO
2 59587 Näiden yhdisteiden valmistusta on kuvattu mm. julkaisussa "Chimie Therapeutique", n:o 4, sivut 290 - 292 (1969), jonka mukaan substituoitu piperatsiini saatetaan reagoimaan 3,4,5 trimetoksikinnamoyylihappohalogenidin kanssa. Tällaisessa menetelässä käytettyjen lähtöaineiden valmistus on hankalaa, joten valmistettavan yhdisteen hinta on melko korkea. Toisena epäkohtana on se, että reaktiossa tapahtuu reagenssien ketjun lohkeamista ja tämä lohjennut ketju liittyy lähtöaineena käytetyn piperatsiinin substituoimattomaan typpiatomiin, jolloin saadaan sivutuotteena disubstituoitu piperatsiini.2,59587 The preparation of these compounds has been described e.g. in "Chimie Therapeutique", No. 4, pages 290-292 (1969), according to which substituted piperazine is reacted with 3,4,5 trimethoxycinnamoyl acid halide. The starting materials used in such a process are difficult to prepare, so the cost of the compound to be prepared is quite high. Another disadvantage is that the chain of reagents is cleaved in the reaction and this cleaved chain is attached to the unsubstituted nitrogen atom of the starting piperazine to give a disubstituted piperazine as a by-product.
Nyt on yllättäen havaittu, että kaavan I mukainen yhdiste voidaan yksinkertaisella tavalla valmistaa käytännöllisesti katsoen ilman ei-toivottuja sivutuotteita saattamalla l-(3,4,5-trimetoksikinna-moyyli)-4-formyylipiperatsiini reagoimaan vesipitoisen kloorivety-hapon kanssa. Keksinnössä käytetyt lähtöaineet ovat kaikki helposti saatavissa kaupallisesti. Lisäksi menetelmä voidaan yksinkertaisella tavalla viedä loppuun eikä sivureaktiot häiritse reaktion kulkua.It has now surprisingly been found that a compound of formula I can be prepared in a simple manner with virtually no undesired by-products by reacting 1- (3,4,5-trimethoxycinnamoyl) -4-formylpiperazine with aqueous hydrochloric acid. The starting materials used in the invention are all readily available commercially. In addition, the process can be completed in a simple manner and the side reactions do not interfere with the course of the reaction.
Seuraavassa on esitetty esimerkki keksinnön mukaisen menetelmän soveltamiseksi.The following is an example of the application of the method according to the invention.
Esimerkki (3,4,5-tr imetoksikinnamoyyli)piperatsiiniExample (3,4,5-trimethoxycinnamoyl) piperazine
Liuokseen, jossa on 512 g (2 moolia) 3,4,5-trimetoksi-kinnamihapon kloridia 4 litrassa kloroformia, jossa on 252 g (3 moolia) natriumbikarbonaattia, lisätään yhden tunnin kuluessa 228 g (2 moolia) formyylipiperatsiinia, ja seoksen annetaan reagoida kylmänä 6 tuntia. Tämän jälkeen suodatetaan liuos, minkä jälkeen suodos väkevöidään. Absoluuttisesta alkoholista suoritetun toistokitey-tyksen jälkeen saadaan 424 g l-(3,4,5-trimetoksikinnamoyyli)-4-formyylipiperatsiinia.To a solution of 512 g (2 moles) of 3,4,5-trimethoxy-cinnamic acid chloride in 4 liters of chloroform with 252 g (3 moles) of sodium bicarbonate is added 228 g (2 moles) of formylpiperazine within one hour, and the mixture is allowed to react. cold for 6 hours. The solution is then filtered and the filtrate is concentrated. After recrystallization from absolute alcohol, 424 g of 1- (3,4,5-trimethoxycinnamoyl) -4-formylpiperazine are obtained.
Sulamispiste 134°C Saanto 63 % 3 59587 Lämpötilassa 90°C lisätään 6 tunnin aikana suspensio, jossa on 0,32 moolia (106 g) 1-(3,4,5-trimetoksikinnamoyyli)-4-formyyli-piperatsiinia 320 ml:aan 10-prosenttista kloorivedyn vesiliuosta.Melting point 134 ° C Yield 63% 3,59587 At 90 [deg.] C., a suspension of 0.32 mol (106 g) of 1- (3,4,5-trimethoxycinnamoyl) -4-formylpiperazine is added over 6 hours to 320 ml. 10% aqueous hydrogen chloride solution.
Saatu liuos väkevöidään. Absoluuttisesta alkoholista suoritetun toistokiteytyksen jälkeen saadaan 70 % 3,4,5-trimetoksikinna-moyylipiperatsiinin kloorihydraattia.The resulting solution is concentrated. After recrystallization from absolute alcohol, 70% of 3,4,5-trimethoxycinnamoylpiperazine hydrochloride is obtained.
Sulamispiste 192°C Saanto 64 % f i i iMelting point 192 ° C Yield 64% f i i i
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI793712A FI59587C (en) | 1972-06-15 | 1979-11-27 | NYTT FOERFARANDE FOER FRAMSTAELLNING AV PIPERAZINDERIVAT |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI171272 | 1972-06-15 | ||
| FI171272 | 1972-06-15 | ||
| FI793712A FI59587C (en) | 1972-06-15 | 1979-11-27 | NYTT FOERFARANDE FOER FRAMSTAELLNING AV PIPERAZINDERIVAT |
| FI793712 | 1979-11-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI793712A FI793712A (en) | 1979-11-27 |
| FI59587B FI59587B (en) | 1981-05-29 |
| FI59587C true FI59587C (en) | 1981-09-10 |
Family
ID=26156509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI793712A FI59587C (en) | 1972-06-15 | 1979-11-27 | NYTT FOERFARANDE FOER FRAMSTAELLNING AV PIPERAZINDERIVAT |
Country Status (1)
| Country | Link |
|---|---|
| FI (1) | FI59587C (en) |
-
1979
- 1979-11-27 FI FI793712A patent/FI59587C/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI59587B (en) | 1981-05-29 |
| FI793712A (en) | 1979-11-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: DELALANDE S.A. |