BE624723A - - Google Patents

Info

Publication number
BE624723A
BE624723A BE624723DA BE624723A BE 624723 A BE624723 A BE 624723A BE 624723D A BE624723D A BE 624723DA BE 624723 A BE624723 A BE 624723A
Authority
BE
Belgium
Prior art keywords
derivatives
piperazine
tri
preparation
pip
Prior art date
Application number
Other languages
French (fr)
Publication of BE624723A publication Critical patent/BE624723A/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

       

   <Desc/Clms Page number 1> 
 
 EMI1.1 
 w vu a pi. 
 EMI1.2 
 



  1 il Le brevet 601.;94 et rapport  à 468 dérivés nOvt&ux.4. 



  1* pip4gattab répbn6nt à 16 fortulé général  
 EMI1.3 
 
 EMI1.4 
 dan. l'q'11t à .pr48tn" un .to.. 4'h1droc\.' ou un .\om. a-halo,i...e ttouvant Oh position otho. Mita Ou p.ra. 



  . te brevet de petff#âtiônne #nt 614-177 conoorne des gélavigu dirtvil de a. pip't'Iin. do tOJl" 0444rble i 

 <Desc/Clms Page number 2> 

 
 EMI2.1 
 
 EMI2.2 
 où &, désigna un radical alkyl. ou alkox7. 



  R2 .t un atome d'hydrogène, un radical alkyle ou tlkoxyt n1# R2 et l pouvant se trouver dan* une position quelconque dur le noyau bons4nique. 



  I.< présent brevet de perfectionnement ne rapporte à 4.   nouveaux     dérivés   de la pipérasion de   formula générale   
 EMI2.3 
 
 EMI2.4 
 dans laquelle RIO R2 et R3 représentent plus partieulièresogt des radicaux méthyle pouvant se trouver dans une position quelconque sur le noyau benzénique  Il se rapport* éfaletn à 
 EMI2.5 
 la préparation de ces dérivés $ins: que de leurs sel* d'acidts minéraux ou organiques. 
 EMI2.6 
 



  Comme les dérivés des brevets 6010394 et 6l.li", le* substances préparées selon le prêtent perfectionnement -- '¯i possèdent une activité antitottx considérable, ils sont tri. p*U 2: toxiques et présentent l'avantage de ne pas   provoquer   de   @   toxicomanie. 



     On   prépare ces produite   selon   le   procédé   décrit   dans     -le   
 EMI2.7 
 brevet 601,394, c'est-à-dire par réaction d'une 1-(Rl Bot IL #" phényl)Wpipéra2ine avec le 1,2*poxy-3-hydroxy-propanes Rt 112 et IL ayant la même signification que plua haut. 



  1,00 exempIO4 outvante muitnnt le prient p'tltt1 iKHt sans lue limiter in aucun  taxons      

 <Desc/Clms Page number 3> 

 
 EMI3.1 
 Exemple je Préparation de la M dnydroxprotyl3..nipdrazine. 



  4 29 a de 1-(2r,6-trim,thylphdny3).pipdreaine porto à environ 7000, on ajoute lentement et avec agitation 18 g ai l,2-époxy-3-hydroxy-propane. La température du milieu réaction  nul s'élève spontanément Jusqu'à 140*C. On le refroidit de manière à maintenir la température vers 100"HO'Ct puis on le 
 EMI3.2 
 laisse reposer pendant une heure. 
 EMI3.3 
 



  On distille sous vide poussé et on recueille 24 a a# l-(2t4t6-tri!aëthylphényl)''4''(2t3-dihydroxyprotyl)-pif'erazine Point d'ébullition de la baget e xx"CCle1 MA . 



  Par transformation en nonochlorfcydratet on obtient, après reorietalliatttion à partir d'ethsnolt 2C ig de produit. 



  Point de fusion du Mnochlorhydrtet 195*Ct . Préparation de la l-0.4.?-tri).ethylrhl}.4-(?.. 



  !: 4.ypï'ofy.)-.p?'" :! Selon la méthode de l'exemple 10 on obtient, à ') partir de 20,4 e de a-(3r4, trindthylphdnyl)wpipâraxinc et if* 12 ff dé ,Z dPoxY-3-h,Ydroxy-propaeat, 21,6 g da 1-(394#5- ##triméthylphényl)-4-(2,3-dihjcdroxypropyl)-pi.pérazine. 



  : Point d'ébullition de la batiei 2Q2*2tJ°'wA,l3. am Re- 
 EMI3.4 
 
 EMI3.5 
 ' Par transformation en diçhlorby4ratob on obtient, après .'eorixttiliae.tioa partir d'éthanol, 20,2 g de produit. 



  Point de fusion du dichlorhydrttet g0*C. 



  Pour préparer cas composés, on s utilisé comme 
 EMI3.6 
 produits de départ l'une des substances nouvelles suivantes 
 EMI3.7 
   #(2y,6tri,m6thylphérxl)..pip6rczine (point d'ebullutiom 104-105*0/0,05 mm Hg)   1-(3#4t5-trtméthylphéiiyi)-pip dr zin* (point d'ibulaitiona 144'4Oy mm iï8) 
 EMI3.8 
 Ces deux produite intermédiaires sont préparée selon 
 EMI3.9 
 tee procédés connus, par exemple 

 <Desc/Clms Page number 4> 

 
 EMI4.1 
 . en chautfant Mn 41Aft6@ a41oir d de thanol 1Q . .di4a phl9rhy4fqtg du 41r1v' t'.Íih11Í Approprié do l'aniline (et'l'ro4RD , M. WICK!R, J''Che.'OQ'Ji,(54)t\5Jf). 



  ..n .hff.nt .&lAn6' éq1MG\6e"1ir' d'un halol'nb1dr.t. de chauffant un mélaniro et 4-4 46VVé tri.'thl1Í approprié de l'nil1ntt # pr4penço 4'Qn alcool .liph&i1\' o d9 carbQn'e 4. 9d1 (V, PgEpa çt Z. BEK. 0011, Çeoçhoolqvak 8h..tço."n'4.(19'4)talI),



   <Desc / Clms Page number 1>
 
 EMI1.1
 w saw a pi.
 EMI1.2
 



  1 he patent 601.; 94 and compared to 468 derivatives nOvt & ux. 4.



  1 * pip4gattab repbn6nt to 16 general fortulé
 EMI1.3
 
 EMI1.4
 dan. l'q'11t to .pr48tn "a .to .. 4'h1droc \. ' or a. \ om. a-halo, i ... e ttouvant Oh position otho. Mita Ou p.ra.



  . the patent of petff # âtiônne #nt 614-177 conoorne of the gelavigu dirtvil of a. pip't'Iin. do tOJl "0444rble i

 <Desc / Clms Page number 2>

 
 EMI2.1
 
 EMI2.2
 where & denotes an alkyl radical. or alkox7.



  R2 .t a hydrogen atom, an alkyl or tlkoxyt n1 # R2 and l can be found in any position in the bons4nic ring.



  I. <this improvement patent does not relate to 4. new derivatives of piperasion of general formula
 EMI2.3
 
 EMI2.4
 in which R10 R2 and R3 represent more particularly methyl radicals which can be found in any position on the benzene ring It refers * efaletn to
 EMI2.5
 the preparation of these derivatives $ ins: that of their salts * of mineral or organic acids.
 EMI2.6
 



  Like the derivatives of patents 6010394 and 61.li ", the * substances prepared according to the improvement - '¯i have a considerable antitottx activity, they are tri. P * U 2: toxic and have the advantage of not causing of @ drug addiction.



     These products are prepared according to the process described in -the
 EMI2.7
 patent 601,394, i.e. by reacting a 1- (Rl Bot IL # "phenyl) Wpipéra2ine with 1,2 * poxy-3-hydroxy-propanes Rt 112 and IL having the same meaning as above .



  1,00 exempIO4 outvante muitnnt pray p'tltt1 iKHt without limiting in any taxa

 <Desc / Clms Page number 3>

 
 EMI3.1
 Example I Preparation of M dnydroxprotyl3..nipdrazine.



  429 a of 1- (2r, 6-trim, thylphdny3) pipdreaine port to about 7000, added slowly and with stirring 18 g of 1,2-epoxy-3-hydroxy-propane. The temperature of the zero reaction medium spontaneously rises to 140 ° C. It is cooled so as to maintain the temperature around 100 "HO'Ct then it is
 EMI3.2
 let sit for an hour.
 EMI3.3
 



  Distilled under high vacuum and collected 24 a # l- (2t4t6-tri! Aëthylphenyl) '' 4 '' (2t3-dihydroxyprotyl) -pif'erazine Boiling point of the baget e xx "CC11 MA.



  By transformation into nonochlorfcydratet one obtains, after reorietalliatttion from ethsnolt 2C ig of product.



  Melting point of Mnochlorhydrtet 195 * Ct. Preparation of l-0.4.? - tri) .ethylrhl} .4 - (? ..



  !: 4.ypï'ofy.) -. P? '":! According to the method of example 10 we obtain, at') from 20.4 e of a- (3r4, trindthylphdnyl) wpipâraxinc and if * 12 ff de, Z dPoxY-3-h, Ydroxy-propaeat, 21.6 g of 1- (394 # 5- ## trimethylphenyl) -4- (2,3-dihjcdroxypropyl) -pi.perazine.



  : Boiling point of the batiei 2Q2 * 2tJ ° 'wA, l3. am Re-
 EMI3.4
 
 EMI3.5
 'By transformation into dichlorby4ratob, after .'eorixttiliae.tioa from ethanol, 20.2 g of product are obtained.



  Melting point of the dihydrochloride and g0 * C.



  To prepare compound cases, we used as
 EMI3.6
 starting materials one of the following new substances
 EMI3.7
   # (2y, 6tri, m6thylphérxl) .. pip6rczine (boiling point 104-105 * 0 / 0.05 mm Hg) 1- (3 # 4t5-trtmethylphéiiyi) -pip dr zin * (ibulaitiona point 144'4Oy mm iï8)
 EMI3.8
 These two intermediate products are prepared according to
 EMI3.9
 known methods, for example

 <Desc / Clms Page number 4>

 
 EMI4.1
 . en chautfant Mn 41Aft6 @ a41oir d de thanol 1Q. .di4a phl9rhy4fqtg du 41r1v 't'.Íih11Í Appropriate for aniline (et'l'ro4RD, M. WICK! R, J''Che.'OQ'Ji, (54) t \ 5Jf).



  ..n .hff.nt. & lAn6 'éq1MG \ 6e "1ir' of a halol'nb1dr.t. of heating a melaniro and 4-4 46VVé tri.'thl1Í appropriate of the nil1ntt # pr4penço 4'Qn alcohol. liph & i1 \ 'o d9 carbQn'e 4. 9d1 (V, PgEpa çt Z. BEK. 0011, Çeoçhoolqvak 8h..tço. "n'4. (19'4) talI),

Claims (1)

EMI5.1 EMI5.1 11 1 in !toavw<nuc dérivé 4. la. p1p6ral1ne ,6pon4&t . la. formula général EMI5.2 eu R1, R2 et R3 représentent des radicaux néthyle pouvant se trouver dans una position quelconque sur le noyau benzénique, 2 Sale 4'acide. minéraux ou organiques préparés à partir des dérivée de la pinpérazine définis au 1 . 11 1 in! Toavw <derivative nuc 4. la. p1p6ral1ne, 6pon4 & t. the. general formula EMI5.2 or R1, R2 and R3 represent nethyl radicals which may be in any position on the benzene ring, 2 Sale 4'acid. minerals or organic prepared from the derivatives of pinperazine defined in 1. 3 Procédé de préparation de dérivés de la pipérazine définis au 1 , caractérisé en ce que l'on fait réagir le 1,2-époxy- EMI5.3 3-hydroxy-propane avec une 1^(Ra,R,R3.phGny1)pip4xazine, R1,R2 et R3 ayant la même signification qu'au l , 4 En tant que dérivés nouveaux de la pipérazinel EMI5.4 1(2,r6^trimdthylphErr1)..4^(2r5-d,hyxaxypxapyl)-pipéraxiai. ,.( , e r 5^tximd thrlphényl )..,° ( 2, 3 xdihydxoxyprapyl )pipérazint, S* En tant que produite nouveaux$ l-(2,4|6-triméthylph inyl)i.pipérazine. 3 Process for the preparation of piperazine derivatives defined in 1, characterized in that the 1,2-epoxy- EMI5.3 3-hydroxy-propane with a 1 ^ (Ra, R, R3.phGny1) pip4xazine, R1, R2 and R3 having the same meaning as in 1.4 As new derivatives of piperazinel EMI5.4 1 (2, r6 ^ trimdthylphErr1) .. 4 ^ (2r5-d, hyxaxypxapyl) -piperaxiai. ,. (, e r 5 ^ tximd thrlphenyl) ..., ° (2, 3 xdihydxoxyprapyl) piperazine, S * As a new product $ 1- (2,4 | 6-trimethylphyl) i.piperazine. 1(3 rr5^tri.méthy3,phnyl j-pip$razine, 1 (3 rr5 ^ tri.methyl3, phnyl j-pip $ razine,
BE624723D BE624723A (en)

Publications (1)

Publication Number Publication Date
BE624723A true BE624723A (en)

Family

ID=196282

Family Applications (1)

Application Number Title Priority Date Filing Date
BE624723D BE624723A (en)

Country Status (1)

Country Link
BE (1) BE624723A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993016056A1 (en) * 1992-02-14 1993-08-19 Dompé Farmaceutici S.P.A. 3-(piperazin-1-yl)-propane-1,2-diol n-oxydes and n,n'-dioxides
CN110198932A (en) * 2017-01-26 2019-09-03 东曹株式会社 Alkanolamine, anti-friction agent and lubricant oil composite

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993016056A1 (en) * 1992-02-14 1993-08-19 Dompé Farmaceutici S.P.A. 3-(piperazin-1-yl)-propane-1,2-diol n-oxydes and n,n'-dioxides
CN110198932A (en) * 2017-01-26 2019-09-03 东曹株式会社 Alkanolamine, anti-friction agent and lubricant oil composite
CN110198932B (en) * 2017-01-26 2023-04-07 东曹株式会社 Alkanolamine, friction reducer, and lubricating oil composition

Similar Documents

Publication Publication Date Title
US2208485A (en) Process for the manufacture of disubstituted carbamic acid esters of phenols containing a basic substituent
JPH04500219A (en) Substituted isoxazolidines and isoxazolines
BE624723A (en)
US2542466A (en) Cyclohexyl-phenyl-aminoalkylketones and their production
BE1010095A3 (en) METHOD OF PREPARATION OF ACID 2- [2- [4 - [(4-Chlorophenyl) phenylmethyl] -1-PIPERAZINYL] ETHOXY] acetic acid AND ITS SALTS.
Singer et al. Relative reactivities of certain 2-and 2, 6-substituted piperidines
US1988501A (en) Preparation of aryl thioglycollic acids
Venkov et al. Synthesis of unsymmetrical β-enamino ketones
DE19801597A1 (en) 1-Aryl-4-arylethyl-piperazine derivative preparation in high yield from aryl-piperazine and aryl olefin, used as drug intermediate
JPH01313457A (en) Production of n-(3&#39;, 4&#39;-dimethoxy-cinnamoyl)- anthranylic acid
US3420827A (en) Process for making 4,4-dimethyl-3-butenyl methyl ketones,intermediates therefor and the said intermediates
US2336093A (en) 1-o-hydroxyphenoxy-3-alkoxy-2-propanols and/or-2-propanones and their manufacture
US2479815A (en) Hydrogenation products of n-phenyl-3, 5-diethyl-2-propyldihydropyridine
KR20060124917A (en) Method of preparing 1,2-benzisothiazolin-3(2h)-one
US2123653A (en) Process for the manufacture of
US3116297A (en) Process for the preparation of phenylpyridylalkylamines
US2129294A (en) 2-amino-6-piperidyl-pyridines
US2798873A (en) Coxnx
US1979351A (en) 3, 6 diamino 2-alkyl pyridine and process for producing the same
Frangatos et al. The synthesis of 10-substituted phenoxazines
SU741796A3 (en) Method of preparing substituted n-/2-(furyl-2)-ethyl/-propynylamines or their salts, or their optical isomers
DE4103968A1 (en) METHOD FOR PRODUCING SULFATOBETAINES
US2062680A (en) 4.6-diamino 2-alkyl pyridines and processes for producing the same
BR112014032934B1 (en) Process for Preparation of Pyridine N-Oxides
Stevens et al. CCCLVIII.—Action of the Grignard reagent upon amino-nitriles