PL94801B1 - METHOD OF MAKING 2-AMINOMETHYLPYROLIDINE - Google Patents
METHOD OF MAKING 2-AMINOMETHYLPYROLIDINE Download PDFInfo
- Publication number
- PL94801B1 PL94801B1 PL1975178472A PL17847275A PL94801B1 PL 94801 B1 PL94801 B1 PL 94801B1 PL 1975178472 A PL1975178472 A PL 1975178472A PL 17847275 A PL17847275 A PL 17847275A PL 94801 B1 PL94801 B1 PL 94801B1
- Authority
- PL
- Poland
- Prior art keywords
- aminomethylpyrrolidine
- benzyl
- catalytic
- formula
- aminomethylpyrolidine
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- 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
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania 2-aminometylopirolidyny o wzorze 1 i jej soli addy¬ cyjnych z kwasami.Znany jest sposób wytwarzania aminometylopiro- lidyny z prolinamidu z wydajnoscia 50%. Taka wy¬ dajnosc w przemysle nie jest zadowalajaca.Obecnie stwierdzono, ze mozna powiekszyc wydaj¬ nosc do okolo 75% zmieniajac surowiec wyjsciowy na N-benzylo-2-nitrometylopirolidyne.Sposób wytwarzania 2-aminometylopirolidyny przedstawiony na schemacie charakteryzuje sie tym, ze poddaje sie redukcji katalitycznej lub najpierw chemicznej a nastepnie katalitycznej, N-benzylo-2- -nitixmetyleaijopiirolidyne o wzorze 2.Redukcji mozna dokonac za pomoca metalu, ta¬ kiego jak zelazo lub cynk w kwasie, takim jak solny lub octowy lub za pomoca wodoru w obecnosci kata¬ lizatora, takiego jak nikiel Raneya, pallad na weglu, czern platynowa, itp. Uwodornianie przeprowadza sie przy cisnieniu od atmosferycznego do 150 atmo¬ sfer.Otrzymana 2-aminometylopirolidyne mozna prze¬ prowadzic w sól z kwasami nieorganicznymi, takimi jak solny, bromowodorowy lub siarkowy lub organi¬ cznymi, takimi jak szczawiowy, winowy, maleinowy, itp.Zaleta sposobu wedlug wynalazku jest wysoka czy¬ stosc produktu. Wysoka czystosc 2-aminometylópiro- lidyny jest cecha bardzo istotna, poniewaz zwiazek ten stosuje sie jako przejsciowy w syntezie zwiazków 2 o atrakcyjnych wlasciwosciach farmakodynamicz- nych.Przyklad. Do autoklawu o pojemnosci 1 litra wprowadza sie 61 g N-benzylo-2-nitrometylenopiro- lidyny, 300 m etanolu, etanolowy roztwór chlorowo¬ doru, w takiej ilosci, by liczba moli chlorowodoru byla dwukrotnie wieksza od liczby moli N-benzylo- -2-nitrometylenopirolidyny, okolo 150 g niklu Raneya i wodór do cisnienia 50 atmosfer. Autoklaw wstrzasa sie w ciagu godziny, a nastepnie dopelnia wodorem do cisnienia 145 atmosfer i w ciagu 5 godzin utrzy¬ muje w 100°C. Po oziebieniu z mieszaniny reakcyjnej odsacza sie nikiel, a przesacz pod zmniejszonym ci¬ snieniem odparowuje do sucha. Pozostalosc rozpu- szcza sie w 200 ml chlorku metylenu, a do roztworu dodaje 40% wodorotlenku sodu lub potasu w postaci pastylek.Po zdekantowaniu warstwe organiczna suszy sie i przesacza, po czym odparowuje rozpuszczalniki. De- stylacja daje 17 g 2-aminometylopirolidyny o tempe¬ raturze wrzenia przy 32 mm Hg 86—89°C. Wydaj¬ nosc 60,7%. PL PL PLThe subject of the invention is a process for the preparation of 2-aminomethylpyrrolidine of the formula I and its acid addition salts. A method for the preparation of aminomethylpyrrolidine from prolinamide with a yield of 50% is known. This industrial yield is unsatisfactory. It has now been found that the yield can be increased to about 75% by changing the starting material to N-benzyl-2-nitromethylpyrrolidine. catalytic reduction, or first chemical followed by catalytic reduction, of N-benzyl-2-nitixmethylai-pyrrolidine of formula II. The reduction can be accomplished with a metal such as iron or zinc in an acid such as hydrochloric acid or acetic acid, or with hydrogen in the presence of a catalytic an lyser such as Raney-nickel, palladium-on-carbon, platinum black, etc. The hydrogenation is carried out at a pressure of from atmospheric to 150 atmospheres. sulfuric or organic, such as oxalic, tartaric, maleic, etc. The advantage of the process according to the invention is the high purity of the product. The high purity of 2-aminomethylpyrrolidine is a very important feature, because this compound is used as an intermediate in the synthesis of compounds 2 with attractive pharmacodynamic properties. Example. 61 g of N-benzyl-2-nitromethylenepyrrolidine, 300 ml of ethanol, and an ethanol solution of hydrogen chloride are introduced into a 1-liter autoclave in such an amount that the number of moles of hydrogen chloride is twice as large as the number of moles of N-benzyl-2 -nitromethylene pyrrolidines, about 150 g of Raney nickel and hydrogen to a pressure of 50 atmospheres. The autoclave is shaken for an hour and then filled with hydrogen to a pressure of 145 atmospheres and kept at 100°C for 5 hours. After cooling, the nickel is filtered off from the reaction mixture and the filtrate is evaporated to dryness under reduced pressure. The residue is dissolved in 200 ml of methylene chloride, and 40% sodium or potassium hydroxide pellets are added to the solution. After decantation, the organic layer is dried and filtered, and the solvents are evaporated. Distillation yields 17 g of 2-aminomethylpyrrolidine, boiling at 32 mmHg, 86°-89°C. Yield 60.7%. PL PL PL
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7407342A FR2263239B1 (en) | 1974-03-04 | 1974-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL94801B1 true PL94801B1 (en) | 1977-08-31 |
Family
ID=9135811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1975178472A PL94801B1 (en) | 1974-03-04 | 1975-03-03 | METHOD OF MAKING 2-AMINOMETHYLPYROLIDINE |
Country Status (33)
| Country | Link |
|---|---|
| JP (1) | JPS5948825B2 (en) |
| AR (1) | AR207350A1 (en) |
| AT (1) | AT358569B (en) |
| BE (1) | BE825728A (en) |
| BG (1) | BG25077A3 (en) |
| CA (1) | CA1047041A (en) |
| CH (1) | CH602636A5 (en) |
| CS (1) | CS179935B2 (en) |
| DD (1) | DD117450A5 (en) |
| DE (1) | DE2506515A1 (en) |
| DK (1) | DK83875A (en) |
| EG (1) | EG11753A (en) |
| ES (1) | ES435139A1 (en) |
| FI (1) | FI750558A (en) |
| FR (1) | FR2263239B1 (en) |
| GB (1) | GB1481251A (en) |
| HK (1) | HK27878A (en) |
| HU (1) | HU169274B (en) |
| IE (1) | IE40685B1 (en) |
| IL (1) | IL46657A (en) |
| LU (1) | LU71947A1 (en) |
| MW (1) | MW875A1 (en) |
| NL (1) | NL7502425A (en) |
| NO (1) | NO145439C (en) |
| OA (1) | OA04856A (en) |
| PH (1) | PH11269A (en) |
| PL (1) | PL94801B1 (en) |
| RO (1) | RO64007A (en) |
| SE (1) | SE401367B (en) |
| SU (1) | SU591139A3 (en) |
| YU (1) | YU36500B (en) |
| ZA (1) | ZA751072B (en) |
| ZM (1) | ZM2775A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4772459A (en) * | 1986-09-09 | 1988-09-20 | Erbamont, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1785124A1 (en) * | 1968-08-13 | 1971-11-11 | Prym Werke William | Zipper |
| JPS5146901B2 (en) * | 1971-08-24 | 1976-12-11 | ||
| CH556836A (en) * | 1971-09-30 | 1974-12-13 | Fratmann Ag | PROCESS FOR THE PREPARATION OF 1-ALKENYL-2-AMINOMETHYLPYRROLIDINES. |
| NL7304089A (en) * | 1972-03-30 | 1973-10-02 | ||
| CH573404A5 (en) * | 1972-07-28 | 1976-03-15 | Inventa Ag |
-
1974
- 1974-03-04 CH CH272675A patent/CH602636A5/xx not_active IP Right Cessation
- 1974-03-04 RO RO7400081539A patent/RO64007A/en unknown
- 1974-03-04 FR FR7407342A patent/FR2263239B1/fr not_active Expired
-
1975
- 1975-01-01 AR AR257827A patent/AR207350A1/en active
- 1975-02-15 DE DE19752506515 patent/DE2506515A1/en active Pending
- 1975-02-18 IL IL46657A patent/IL46657A/en unknown
- 1975-02-20 ZA ZA00751072A patent/ZA751072B/en unknown
- 1975-02-20 BE BE1006472A patent/BE825728A/en not_active IP Right Cessation
- 1975-02-24 GB GB7645/75A patent/GB1481251A/en not_active Expired
- 1975-02-24 IE IE377/75A patent/IE40685B1/en unknown
- 1975-02-25 EG EG93/75A patent/EG11753A/en active
- 1975-02-26 FI FI750558A patent/FI750558A/fi not_active Application Discontinuation
- 1975-02-26 CA CA220,855A patent/CA1047041A/en not_active Expired
- 1975-02-27 ES ES435139A patent/ES435139A1/en not_active Expired
- 1975-02-28 MW MW8/75A patent/MW875A1/en unknown
- 1975-02-28 NL NL7502425A patent/NL7502425A/en not_active Application Discontinuation
- 1975-03-03 SE SE7502340A patent/SE401367B/en not_active IP Right Cessation
- 1975-03-03 PL PL1975178472A patent/PL94801B1/en unknown
- 1975-03-03 DD DD184512A patent/DD117450A5/xx unknown
- 1975-03-03 DK DK83875*#A patent/DK83875A/da not_active Application Discontinuation
- 1975-03-03 PH PH16855A patent/PH11269A/en unknown
- 1975-03-03 SU SU752111076A patent/SU591139A3/en active
- 1975-03-03 AT AT160575A patent/AT358569B/en not_active IP Right Cessation
- 1975-03-03 HU HUSO1136A patent/HU169274B/hu not_active IP Right Cessation
- 1975-03-03 NO NO750699A patent/NO145439C/en unknown
- 1975-03-03 LU LU71947A patent/LU71947A1/xx unknown
- 1975-03-03 BG BG029132A patent/BG25077A3/en unknown
- 1975-03-04 OA OA55432A patent/OA04856A/en unknown
- 1975-03-04 CS CS7500001451A patent/CS179935B2/en unknown
- 1975-03-04 ZM ZM27/75A patent/ZM2775A1/en unknown
- 1975-03-04 JP JP50026947A patent/JPS5948825B2/en not_active Expired
- 1975-03-19 YU YU00676/75A patent/YU36500B/en unknown
-
1978
- 1978-06-01 HK HK278/78A patent/HK27878A/en unknown
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