SU591139A3 - Method of preparing 2-aminomethyl-pyrrolidine - Google Patents
Method of preparing 2-aminomethyl-pyrrolidineInfo
- Publication number
- SU591139A3 SU591139A3 SU752111076A SU2111076A SU591139A3 SU 591139 A3 SU591139 A3 SU 591139A3 SU 752111076 A SU752111076 A SU 752111076A SU 2111076 A SU2111076 A SU 2111076A SU 591139 A3 SU591139 A3 SU 591139A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- pyrrolidine
- aminomethyl
- preparing
- aminomethylpyrrolidine
- mixture
- 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
.1,,.Изобретение относитс к улучшенному способу получени 2-аминометилпирролидина. .1 .. The invention relates to an improved process for the preparation of 2-aminomethylpyrrolidine.
Известен способ получени 2-аминометилпирролидина восстановлением L -про инамидаA method of producing 2-aminomethylpyrrolidine is known by reducing L-pro-inamide.
Недостатком известного способа вл етс применение труднодоступного исходного соединени , стоимость которого высока.A disadvantage of the known method is the use of an inaccessible starting compound, the cost of which is high.
Целью изобретени вл етс упрощение процесса.The aim of the invention is to simplify the process.
Это достигаетс способом получени 2 аминометилпирролидина формулыThis is achieved by a process for the preparation of 2 aminomethylpyrrolidine of the formula
L;L;
CHtHHaCHtHHa
:s: s
Д15D15
заключающемс в том, чтоМ -бензщ1-2-нитthe fact that M is benzsch1-2-nit
ромбтиленпирролидин подвергают катага5т ческому восстановдени1Ю в ттрксутствш в№кел Рене или сол ной кислоты и Рене . Целевой продукт выдел ют. Есш5 uoc-jj становление провод т только в присутствий никел Рене , то перед отделением у деле вого продукта отшепл ют бензильную защитуКаталитическое восстановление лушие осуществл ть под давлением в 50-150 атм «rhombhylene pyrrolidine is subjected to catalysing reduction in the thromosilicus rhenic acid or hydrochloric acid and rene. The desired product is isolated. When eu5 uoc-jj is carried out only in the presence of Rene nickel, then before the separation of a product, the benzyl protection is scattered. Catalytic reduction is best carried out under a pressure of 50-150 atm.
и в присутствии 2 моль сол ной кислоты на 1 моль N -бензи№.2-нитрометиле тирролидина .and in the presence of 2 mol of hydrochloric acid per 1 mol of N-benzene No. 2-nitromethyl tyrrolidine.
Пример. 2-АминометилпирролидинExample. 2-aminomethylpyrrolidine
А. N -Бензилпирролидон-2.A. N-Benzylpyrrolidone-2.
В колбу емкостью 6 л наливают2100 м этанола, затем внос т 138 г натри . В конце реакции смесь охлаждают до 15-2О С и внос т 510 г пирролидона-2. Спирт отгон ют под вакуумом и приливают 2400 мл ксилола. Часть растворител отгон ют дл полного удалени спирта.In a flask with a capacity of 6 liters, 2100 m of ethanol is poured, then 138 g of sodium are added. At the end of the reaction, the mixture is cooled to 15-2 ° C and 510 g of pyrrolidone-2 are introduced. The alcohol is distilled off in vacuo and 2400 ml of xylene are poured. A portion of the solvent was distilled off to completely remove the alcohol.
Смесь довод т до температуры кипени и внос т 759 г хлористого бензила. Выдер сийают 8 ч при температуре кипени (с обратным холодильником), смесь охлаждают, фильтруют. Растворитель отгон ют пой вакуумом и после очистки методом дистил. л иии получают 862 г N -бензилпирролидона-2 .The mixture is brought to a boiling point and 759 g of benzyl chloride are introduced. It is incubated for 8 hours at reflux temperature, the mixture is cooled, filtered. The solvent is distilled off under vacuum and after distillation cleaning. 862 g of N-benzylpyrrolidone-2 are obtained.
Выхор82%;т.Кйп. 148-150 С (23ммрт.Vykhor82%; t.Kyp. 148-150 С (23mmrt.
Б. Н -Бензил-3-нитрометиленпирролидин.B. N-Benzyl-3-nitromethylenepyrrolidine.
Вколбу емкостью 6 л внос т 875 г Ы-бензилпирролидона-2 и 630 г диметипсульфата . После 1,5 ч нагревани смесиIn a flask with a capacity of 6 liters, 875 g of L-benzylpyrrolidone-2 and 630 g of dimetypsulphate are introduced. After 1.5 h of heating the mixture
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 |
|---|---|
| SU591139A3 true SU591139A3 (en) | 1978-01-30 |
Family
ID=9135811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752111076A SU591139A3 (en) | 1974-03-04 | 1975-03-03 | Method of preparing 2-aminomethyl-pyrrolidine |
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 RO RO7400081539A patent/RO64007A/en unknown
- 1974-03-04 FR FR7407342A patent/FR2263239B1/fr not_active Expired
- 1974-03-04 CH CH272675A patent/CH602636A5/xx not_active IP Right Cessation
-
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 CA CA220,855A patent/CA1047041A/en not_active Expired
- 1975-02-26 FI FI750558A patent/FI750558A/fi not_active Application Discontinuation
- 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 BG BG7500029132A patent/BG25077A3/en unknown
- 1975-03-03 PH PH16855A patent/PH11269A/en unknown
- 1975-03-03 PL PL1975178472A patent/PL94801B1/en unknown
- 1975-03-03 LU LU71947A patent/LU71947A1/xx unknown
- 1975-03-03 SU SU752111076A patent/SU591139A3/en active
- 1975-03-03 SE SE7502340A patent/SE401367B/en not_active IP Right Cessation
- 1975-03-03 DK DK83875*#A patent/DK83875A/da not_active Application Discontinuation
- 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 DD DD184512A patent/DD117450A5/xx unknown
- 1975-03-03 AT AT160575A patent/AT358569B/en not_active IP Right Cessation
- 1975-03-04 ZM ZM27/75A patent/ZM2775A1/en unknown
- 1975-03-04 JP JP50026947A patent/JPS5948825B2/en not_active Expired
- 1975-03-04 OA OA55432A patent/OA04856A/en unknown
- 1975-03-04 CS CS7500001451A patent/CS179935B2/en unknown
- 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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