CS195311B2 - Method of producing new enamines - Google Patents
Method of producing new enamines Download PDFInfo
- Publication number
- CS195311B2 CS195311B2 CS763722A CS372276A CS195311B2 CS 195311 B2 CS195311 B2 CS 195311B2 CS 763722 A CS763722 A CS 763722A CS 372276 A CS372276 A CS 372276A CS 195311 B2 CS195311 B2 CS 195311B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- alkyl
- group
- ethyl
- enamines
- methyl
- 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
Vynález se týká způsobu výroby nových . enaminů obecného vzorce I, ?2
RfCH*C-NH-CH2
(I) ve kterém
R znamená alkylovou skupinu s 1 až 4 atomy uhlíku,
Ri představuje alkoxykarbonylovou skupinu s 1 až 4 atomy uhlíku v alkoxylové části a
Rz znamená alkylovou skupinu s 1 až 4 atomy uhlíku, jakož i jejích pravotočivých a levotočivých isomerů, adičních solí s kyselinami a kvartérních amoniových solí.
Sloučeniny podle vynálezu je možno používat například k výrobě sloučenin majících cenné terapeutické vlastnosti.
Sloučeniny podle vynálezu je možno připravit reakcí /З-ketoesterů obecného vzorce Π,
Ri—CHz—C—R2
II o
(Π) ' 2 ve kterém
Ri a Rž mají shora uvedený význam, s racemickými, pravotočivými nebo levotočivými aminy obecného vzorce III, H2N~CH2 SjT (lt)
R ve kterém
R má shora uvedený význam, a na získaný produkt se popřípadě působí minerální nebo organickou kyselinou nebo činidlem vhodným pro· přípravu kvartérní amoniové soli. .
Vynález ilustruje následující příklad provedení, jímž se však rozsah vynálezu v žádném směru neomezuje.
Příklad
Methyl-N- [ l-ethyl-2-pyrrolidylmethyl) -3-aminokrotonáthydrochlorid
Do baňky o objemu 250 ml, opatřené míchadlem, · teploměrem, chladičem a přika3 páva jící nálevkou, se předloží 38,4 g (0,3 mol) N-ethyl-2-aminomethylpyrrolidlnu a kapka kyseliny chlorovodíkové (hustota 1,18). К směsi se pak přikape 34,8 g (0,3 mol) acetoctanu methylnatého, přičemž ke konci přikapávání teplota vystoupí na 54 °C. Reakční směs se nechá za míchání zchladnout na teplotu místnosti, pak se к ní přidá 150 ml methylenchloridu a 5 g síranu hořečnatého, výsledná směs se 1 hodinu míchá, zfiltruje se, rozpouštědlo se odpaří ve vakuu a zbytek se podrobí destilaci. Získá se 55 g (výtěžek 81,1 %) methyl-N-(l-ethyl-2-pyrrolídylmethyl) -3-aminokr otonátu o teplotě varu 132 až 134 °C 400 Pa.
Do kádinky o objemu 500 ml se za míchání předloží 55 g (0,24 mol) methyl-N- (l-ethyl-2-pyrrolidylmethyl)-3-aminokrotonátu, 250 ml acetonu a dostatečné množství ethanolického chlorovodíku к úpravě pH na hodnotu 1. Produkt se nechá vykrystalovat, pak se odfiltruje a vysuší se v sušárně při teplotě 50 °C.
Získá se 60,8 g (výtěžek 95,2 %) methyl-N-(l-ethyl-2-pyrrolidylmethyl)-3-aminokrotonáthydrochloridu o bodu tání 140 °C.
Claims (1)
- Způsob výroby nových enaminů obecného vzorce I, ?2RfCHsC-NH-CHzR ve kterémR znamená alkylovou skupinu s 1 až 4 atomy uhlíku,Ri představuje alkoxykarbonylovou skupinu s 1 až 4 atomy uhlíku v alkoxylové části aRž znamená alkylovou skupinu s 1 až 4 atomy uhlíku, jejich pravotočivých a levotočivých isomerů, edičních solí s kyselinami a kvartérních amoniových solí, vyznačující se tím, že se /З-ketoestery obecného vzorce II,Ri—CH2—C—R2O (П) ve kterémRi a R2 mají shora uvedený význam, nechají reagovat s racemickým, pravotočivým nebo levotočivým aminem obecného vzorce III,.....R ve kterémR má shora uvedený význam, a na získaný produkt se popřípadě působí minerální nebo organickou kyselinou nebo činidlem vhodným pro přípravu kartérní amoniové soli.
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 (1)
| Publication Number | Publication Date |
|---|---|
| CS195311B2 true CS195311B2 (en) | 1980-01-31 |
Family
ID=9156406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS763722A CS195311B2 (en) | 1975-06-12 | 1976-06-04 | Method of producing new enamines |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US4077976A (cs) |
| JP (1) | JPS6016414B2 (cs) |
| AR (1) | AR211016A1 (cs) |
| AT (1) | AT361461B (cs) |
| AU (1) | AU498622B2 (cs) |
| BE (1) | BE842060A (cs) |
| BG (1) | BG34184A3 (cs) |
| CA (1) | CA1069911A (cs) |
| CH (1) | CH615420A5 (cs) |
| CS (1) | CS195311B2 (cs) |
| DE (1) | DE2623076A1 (cs) |
| DK (1) | DK260276A (cs) |
| EG (1) | EG13535A (cs) |
| FI (1) | FI63749C (cs) |
| FR (1) | FR2314179A1 (cs) |
| GB (1) | GB1500225A (cs) |
| HK (1) | HK47079A (cs) |
| HU (1) | HU171358B (cs) |
| IE (1) | IE43002B1 (cs) |
| IL (1) | IL49597A (cs) |
| IN (1) | IN142641B (cs) |
| LU (1) | LU75105A1 (cs) |
| MC (1) | MC1103A1 (cs) |
| MW (1) | MW1776A1 (cs) |
| MX (1) | MX3617E (cs) |
| NL (1) | NL7606353A (cs) |
| NO (1) | NO761978L (cs) |
| NZ (1) | NZ181073A (cs) |
| OA (1) | OA05349A (cs) |
| PH (1) | PH13943A (cs) |
| PL (1) | PL106501B1 (cs) |
| PT (1) | PT65166B (cs) |
| RO (1) | RO69115A (cs) |
| SE (1) | SE410791B (cs) |
| SU (1) | SU629874A3 (cs) |
| YU (1) | YU39542B (cs) |
| ZA (1) | ZA763043B (cs) |
| ZM (1) | ZM6676A1 (cs) |
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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