PL106501B1 - Sposob wytwarzania nowych enamin - Google Patents
Sposob wytwarzania nowych enamin Download PDFInfo
- Publication number
- PL106501B1 PL106501B1 PL1976190303A PL19030376A PL106501B1 PL 106501 B1 PL106501 B1 PL 106501B1 PL 1976190303 A PL1976190303 A PL 1976190303A PL 19030376 A PL19030376 A PL 19030376A PL 106501 B1 PL106501 B1 PL 106501B1
- Authority
- PL
- Poland
- Prior art keywords
- group
- formula
- carbon atoms
- alkyl
- alkyl group
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania nowych
enamin o ogólnym wzorze 1, w którym R oznacza grupe
alkilowa o 1—5 atomach wegla, Rx oznacza grupe alkilowa
o 1—5 atomach wegla lub grupe karboksylanu alkilowego
lub tez grupe acylowa, R2 oznacza grupe alkilowa o 1—5 5
atomach wegla lub grupe karboksylanu alkilowego, Ri i R2
moga byc wzajemnie polaczone za posrednictwem grupy
metylenowej, n moze oznaczac liczbe 1—3, jak równiez
ich izomerów prawoskretnych i lewoskretnych, ich soli
addycyjnych z kwasami, czwartorzedowych soli amonio- 10
wych.
Zwiazki te znajduja zastosowanie na przyklad w syntezie
pochodnych benzamidu, uzywanych w lecznictwie jako
srodki przeciwwymiotne i scharakteryzowanych szczególowo
w polskim opisie patentowym nr54435. 15
Sposobem wedlug wynalazku nowe enaminy o wzorze 1,
wytwarza sie przez poddanie reakcji ketonów posiadajacych
mobilny atom wodoru w pozycji o, p-dwuketonów alifa¬
tycznych lub estrów p-dwuketonów z amina o wzorze
ogólnym 2, w którym R i n maja wyzej podane znaczenie. 20
Przyklad ilustruje wynalazek.
Przyklad. Wytworzenie chlorowodorku N- (1-etylo-
2-pirolydylometylo) -3-amino-krotonian metylu.
W kolbie o pojemnosci 250 ml wyposazonej w termo¬
metr, mieszadlo, chlodnice i wkraplacz umieszczono 38,4 g 25
(0,3 mola) N-etylo-2-aminometylopirolidyny, krople kwasu
solnego o gestosci d= l—18 oraz wkroplono 34,8 g (0,3
mola) acetylooctanu metylowego. Przy koncu wkraplania
temperatura wynosila 54 °C. Mieszanine mieszajac pozosta¬
wiono do ochlodzenia do temperatury otoczenia, a nastepnie 30
dodano 150 ml chlorku metylenu i 5 g siarczanu magne¬
zowego. Po godzinnym mieszaniu mieszanine przesaczono>
rozpuszczalnik odparowano pod zmniejszonym cisnieniem,
a pozostalosc przedestylowano. Otrzymano 55 g N- (1-etylo-
-2-pirolidynometylo)-3-amino-krotonianu metylu (wydaj¬
nosc 81,1%). Temperatura wrzenia przy cisnieniu 3 mm
slupa rteci — 132—134 °C.
W zlewce o pojemnosci 500 ml umieszczono 55 g (0,24
mola) N- (l-etylo-2-pirolidylometylo) -3-amino-krotonianu
metylu, 250 ml acetonu i roztwór kwasu solnego w etanolu
w ilosci zapewniajacej pH = 1 calosci. Po wymieszaniu
mieszaniny pozostawiono ja do krystalizacji, a wytracony
produkt odsaczono i wysuszono w suszarce w 50 °C. Otrzy¬
mano 60,8 g chlorowodorku N- (l-etylo-2-pirolidylo-
-metylo)-3-aminokrotonianu metylu, (wydajnosc 95,2%),
temperatura topnienia 140°C.
Claims (2)
1. Sposób wytwarzania nowych enamin o wzorze ogólnym 1, w którym R oznacza grupe alkilowa o 1—5 atomach wegla, Ri oznacza grupe alkilowa o 1—5 atomach wegla lub grupe karboksylanu alkilowego lub tez grupe acylowa, Rz oznacza grupe alkilowa o 1—5 atomach wegla lub grupe karboksylanu alkilowego, Rx i R2 moga byc wzajemnie polaczone za pomoca grupy metylenowej, n oznacza liczbe 1—3 jak równiez ich izomerów prawoskretnych i lewoskret¬ nych, ich woli addycyjnych z kwasami, czwartorzedowych soli amoniowych, znamienny tym, ze poddaje sie reakcji ketony zawierajace mobilny ct-wodór, P-dwuketony alifa- 106 501106 501 3 4 tyczne lub estry P-ketonów z amina o wzorze ogólnym 2,
2. Sposób wedlug zastrz. 1, znamienny tym, ze poddaje w którym n i R maja znaczenie podane uprzednio, po czym sie reakcji N-etylo-2-amino-metylopirolidyne z acetylo- otrzymane zwiazki o wzorze 1 przeprowadza sie ewentualnie octanem metylu, a nastepnie uzyskany zwiazek dzialaniem w sole addycyjne z kwasami organicznymi lub nieorganicz- kwasu solnego przeprowadza w chlorowodorek N-(l-etylo- nymi. 5 2-pirolidylometyIo)-3-amino-krotonian metylu. R2 RrCHr C-NH-(CH2)n-^P i R Wzór 1 H2N-(H2C)n-C I R Wzór 2 LZG Z-d 3 w Pab., zam. 1442-79, nakl. 05+20 egz. Cena 45 zl
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7518344A FR2314179A1 (fr) | 1975-06-12 | 1975-06-12 | Nouvelles enamines et leur procede de preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL190303A1 PL190303A1 (pl) | 1978-07-17 |
| PL106501B1 true PL106501B1 (pl) | 1979-12-31 |
Family
ID=9156406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976190303A PL106501B1 (pl) | 1975-06-12 | 1976-06-10 | Sposob wytwarzania nowych enamin |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US4077976A (pl) |
| JP (1) | JPS6016414B2 (pl) |
| AR (1) | AR211016A1 (pl) |
| AT (1) | AT361461B (pl) |
| AU (1) | AU498622B2 (pl) |
| BE (1) | BE842060A (pl) |
| BG (1) | BG34184A3 (pl) |
| CA (1) | CA1069911A (pl) |
| CH (1) | CH615420A5 (pl) |
| CS (1) | CS195311B2 (pl) |
| DE (1) | DE2623076A1 (pl) |
| DK (1) | DK260276A (pl) |
| EG (1) | EG13535A (pl) |
| FI (1) | FI63749C (pl) |
| FR (1) | FR2314179A1 (pl) |
| GB (1) | GB1500225A (pl) |
| HK (1) | HK47079A (pl) |
| HU (1) | HU171358B (pl) |
| IE (1) | IE43002B1 (pl) |
| IL (1) | IL49597A (pl) |
| IN (1) | IN142641B (pl) |
| LU (1) | LU75105A1 (pl) |
| MC (1) | MC1103A1 (pl) |
| MW (1) | MW1776A1 (pl) |
| MX (1) | MX3617E (pl) |
| NL (1) | NL7606353A (pl) |
| NO (1) | NO761978L (pl) |
| NZ (1) | NZ181073A (pl) |
| OA (1) | OA05349A (pl) |
| PH (1) | PH13943A (pl) |
| PL (1) | PL106501B1 (pl) |
| PT (1) | PT65166B (pl) |
| RO (1) | RO69115A (pl) |
| SE (1) | SE410791B (pl) |
| SU (1) | SU629874A3 (pl) |
| YU (1) | YU39542B (pl) |
| ZA (1) | ZA763043B (pl) |
| ZM (1) | ZM6676A1 (pl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4370335A (en) * | 1982-02-02 | 1983-01-25 | Mcneilab, Inc. | Antisecretory 4-diphenylmethyl-1-[(oxoalkyl)imino]methyl-piperidines and their derivatives |
| ES2017932B3 (es) * | 1985-12-23 | 1991-03-16 | Dr Lo Zambeletti S P A | Compuestos azaciclicos, procedimientos de su preparacion y su uso como farmacos. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3878223A (en) * | 1973-03-12 | 1975-04-15 | Abbott Lab | N-Substituted acrylamides |
-
1975
- 1975-06-12 FR FR7518344A patent/FR2314179A1/fr active Granted
-
1976
- 1976-05-17 IL IL49597A patent/IL49597A/xx unknown
- 1976-05-20 MC MC761195A patent/MC1103A1/xx unknown
- 1976-05-21 ZA ZA763043A patent/ZA763043B/xx unknown
- 1976-05-21 BE BE1007405A patent/BE842060A/xx not_active IP Right Cessation
- 1976-05-22 DE DE19762623076 patent/DE2623076A1/de not_active Withdrawn
- 1976-05-24 AR AR263375A patent/AR211016A1/es active
- 1976-05-27 IN IN927/CAL/1976A patent/IN142641B/en unknown
- 1976-05-27 AU AU14361/76A patent/AU498622B2/en not_active Expired
- 1976-05-28 YU YU1319/76A patent/YU39542B/xx unknown
- 1976-06-01 AT AT400276A patent/AT361461B/de not_active IP Right Cessation
- 1976-06-01 PT PT65166A patent/PT65166B/pt unknown
- 1976-06-01 SU SU762362104A patent/SU629874A3/ru active
- 1976-06-01 RO RO7686313A patent/RO69115A/ro unknown
- 1976-06-01 IE IE1168/76A patent/IE43002B1/en unknown
- 1976-06-02 EG EG327/76A patent/EG13535A/xx active
- 1976-06-03 ZM ZM66/76A patent/ZM6676A1/xx unknown
- 1976-06-04 CS CS763722A patent/CS195311B2/cs unknown
- 1976-06-04 BG BG7633363A patent/BG34184A3/xx unknown
- 1976-06-04 NZ NZ181073A patent/NZ181073A/xx unknown
- 1976-06-07 PH PH18544A patent/PH13943A/en unknown
- 1976-06-08 LU LU75105A patent/LU75105A1/xx unknown
- 1976-06-08 SE SE7606426A patent/SE410791B/xx not_active IP Right Cessation
- 1976-06-09 CA CA254,483A patent/CA1069911A/en not_active Expired
- 1976-06-09 MX MX76293U patent/MX3617E/es unknown
- 1976-06-09 OA OA55846A patent/OA05349A/xx unknown
- 1976-06-09 NO NO761978A patent/NO761978L/no unknown
- 1976-06-10 JP JP51068623A patent/JPS6016414B2/ja not_active Expired
- 1976-06-10 GB GB24113/76A patent/GB1500225A/en not_active Expired
- 1976-06-10 MW MW17/76A patent/MW1776A1/xx unknown
- 1976-06-10 PL PL1976190303A patent/PL106501B1/pl unknown
- 1976-06-11 FI FI761679A patent/FI63749C/fi not_active IP Right Cessation
- 1976-06-11 HU HU76SO00001172A patent/HU171358B/hu unknown
- 1976-06-11 CH CH745176A patent/CH615420A5/fr not_active IP Right Cessation
- 1976-06-11 NL NL7606353A patent/NL7606353A/xx not_active Application Discontinuation
- 1976-06-11 US US05/694,877 patent/US4077976A/en not_active Expired - Lifetime
- 1976-06-11 DK DK260276A patent/DK260276A/da not_active Application Discontinuation
-
1979
- 1979-07-12 HK HK470/79A patent/HK47079A/xx unknown
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