IL41522A - Preparation of n-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-ethylsulphonyl-benzamide - Google Patents
Preparation of n-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-ethylsulphonyl-benzamideInfo
- Publication number
- IL41522A IL41522A IL41522A IL4152273A IL41522A IL 41522 A IL41522 A IL 41522A IL 41522 A IL41522 A IL 41522A IL 4152273 A IL4152273 A IL 4152273A IL 41522 A IL41522 A IL 41522A
- Authority
- IL
- Israel
- Prior art keywords
- ethyl
- ethylsulphonyl
- benzamide
- preparation
- methoxy
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Preparation The invention relate s to the preparation of benzamide and its pharmac eutically acc eptable addition salts with suitable mineral or organic acids as as the quaternary ammonium salts obtained from this benzamide by reaction with an aliphatic or aromatic alkylation According to the a method for the preparation of the indicated compounds compris es reacting pyrrolidine with pho sphorus oxychloride and ing the resultant phosphoramide with a solution of benzoic m ethyls benzamide pos s es s es valuable pharmacological properties particularly as an emetic and psychotropic The method according to the invention proc eeds in the following manner 3 4 The reactions shown above can be performed in suitable solvents in which the reaction mixtur e is heated to the r eflux The use of pyridine as the solvent offer s the advantage that the hydrochloride of the phosphoramide need not be However according to another aspect of the a ris new intermediary phosphoramide may be Several examples of carrying out the method according to the invention will now be described in EXAMPLE 1 hydrochloride 27g arninomethylpyrrolidine are dissolved in 560ml pyridine in a reaction vessel of 1 litre A solution of lg phosphorus oxychloride in 65ml pyridine is introduced at ambient temperature and the reactants are stirred for half an benzoic acid are then added and the reaction mixture is boiled under reflux for four hours Following the resultant the pyridine is evaporated off under vacuum and the residue is taken up in 300ml water and 40ml hydrochloric in order to remove possible remains of unreacted benzoic The solution is made alkaline with an alkali and is extracted with methylene The organic layer is filtered and evaporatedin The residue is dissolved in 20ml acetone and the hydrochloride is pitated by the addition of hydrochloric It is washed with 10ml ethanol and dried in a drying oven at I6g of N benzamide hydrochloride are with a melting point of This product is twice r ecrystallised from giving lOg of the benzamide hydrochloride with a melting point of its purity analysed with perchloric acid is EXAMPLE 2 A solution of pyrrolidine in 1 toluene is placed in a 250ml reaction lg phosphorus oxychloride dissolved in 40ml toluene is added at ambient temperature After stirring for two hours at ambient the precipitate formed is filtered washed and hydrochloride with a melting point of is The hydrochloride thus obtained is dissolved in 350ml water and the solution is made alkaline with an alkali This solution is then extracted with The organic layer is dried over potassium carbonate and evaporated under phosphoramide is its purity analysed with perchloric acid is The phosphorami obtained can then be condensed with a solution of benzoic insufficientOCRQuality
Claims (6)
1. A method for the preparation of N- ( 1- ethyl- 2-pyrrolidylmethyl)- 2- methoxy- 5- ethylsulphonyl- benzamide having the formula and its pharmaceutically acceptable addition salts with suitable mineral or organic acids, also its quaternary ammonium salts, comprising reacting N- ethyl- ^ - aminomethyl- pyrrolidine with phosphorus oxychloride, and condensing the resultant phosphoramide with a solution of 2- ethoxy- 5- ethylsulphonyl- benzoic acid.
2. A method according to claim 1, which pyridine is used as solvent.
3. A method for the preparation of N- ( 1- ethyl- 2-pyrrolidylrnethyl)-2-methoxy- 5- ethylsulphonyl- benzamide substantially as hereinbefore described with reference to Example I.
4. N- ( 1- ethyl- 2-pyrrolidylmethyl)- 2- methoxy- 5- ethylsulphonyl-benzamide and its pharmaceutically acceptable addition salts with suitable mineral or organic acids, also its quaternary ammonium salts, whenever prepared by a method according to any preceding claim. I
5. e.
6. A method for the preparation of Ν-'-,^τΝ-*11- (N- ethyl- c - methylpyrrolidine)- phosphoramide substantially as hereinbefore described with reference to Example II. XOHEN ZEDE & SPISBACH P.0. Box 33116 , Tel-Aviv Attorneys for Applicant
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1080272A CH565149A5 (en) | 1972-07-19 | 1972-07-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41522A0 IL41522A0 (en) | 1973-04-30 |
| IL41522A true IL41522A (en) | 1977-11-30 |
Family
ID=4367011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41522A IL41522A (en) | 1972-07-19 | 1973-02-13 | Preparation of n-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-ethylsulphonyl-benzamide |
Country Status (29)
| Country | Link |
|---|---|
| JP (2) | JPS4935377A (en) |
| KR (1) | KR780000089B1 (en) |
| AR (1) | AR194145A1 (en) |
| AT (1) | AT319932B (en) |
| AU (1) | AU471164B2 (en) |
| BE (1) | BE793871A (en) |
| BG (1) | BG20347A3 (en) |
| CA (1) | CA976974A (en) |
| CH (1) | CH565149A5 (en) |
| CS (1) | CS174865B2 (en) |
| DD (1) | DD102380A5 (en) |
| DE (1) | DE2257624A1 (en) |
| EG (1) | EG11435A (en) |
| ES (1) | ES409348A1 (en) |
| FR (1) | FR2192820B1 (en) |
| GB (1) | GB1394409A (en) |
| HU (1) | HU167514B (en) |
| IE (1) | IE37363B1 (en) |
| IL (1) | IL41522A (en) |
| LU (1) | LU66787A1 (en) |
| MC (1) | MC961A1 (en) |
| NL (1) | NL7215710A (en) |
| OA (1) | OA04313A (en) |
| PH (1) | PH9390A (en) |
| PL (1) | PL82470B1 (en) |
| RO (1) | RO62350A (en) |
| YU (1) | YU36499B (en) |
| ZA (1) | ZA73537B (en) |
| ZM (1) | ZM1773A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1151533B (en) * | 1982-03-29 | 1986-12-24 | Ravizza Spa | PROCEDURE FOR THE PREPARATION OF P. CHLOROFENOSSIACETIL-PIPERONILPIPERAZINA |
| WO1991017144A1 (en) * | 1990-05-02 | 1991-11-14 | Yoshitomi Pharmaceutical Industries, Ltd. | Amide compound, pharmaceutical use thereof and novel 1-substituted pyrrolidinemethyl-amines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4940459B1 (en) * | 1970-12-21 | 1974-11-02 |
-
0
- BE BE793871D patent/BE793871A/en not_active IP Right Cessation
-
1972
- 1972-07-19 CH CH1080272A patent/CH565149A5/xx not_active IP Right Cessation
- 1972-11-20 NL NL7215710A patent/NL7215710A/xx unknown
- 1972-11-22 AR AR245248A patent/AR194145A1/en active
- 1972-11-24 HU HURE521A patent/HU167514B/hu unknown
- 1972-11-24 PL PL1972159072A patent/PL82470B1/pl unknown
- 1972-11-24 DE DE2257624A patent/DE2257624A1/en active Pending
- 1972-11-30 BG BG022005A patent/BG20347A3/en unknown
- 1972-12-01 RO RO73014A patent/RO62350A/ro unknown
- 1972-12-05 YU YU03015/72A patent/YU36499B/en unknown
- 1972-12-06 AT AT1038972A patent/AT319932B/en not_active IP Right Cessation
- 1972-12-06 CS CS8355A patent/CS174865B2/cs unknown
- 1972-12-06 ES ES409348A patent/ES409348A1/en not_active Expired
- 1972-12-11 FR FR7244002A patent/FR2192820B1/fr not_active Expired
- 1972-12-15 MC MC1024A patent/MC961A1/en unknown
- 1972-12-28 DD DD167945A patent/DD102380A5/xx unknown
-
1973
- 1973-01-03 LU LU66787A patent/LU66787A1/xx unknown
- 1973-01-12 OA OA54805A patent/OA04313A/en unknown
- 1973-01-18 CA CA161,588A patent/CA976974A/en not_active Expired
- 1973-01-24 ZA ZA730537A patent/ZA73537B/en unknown
- 1973-01-26 AU AU51514/73A patent/AU471164B2/en not_active Expired
- 1973-02-06 JP JP48014354A patent/JPS4935377A/ja active Pending
- 1973-02-12 ZM ZM17/73A patent/ZM1773A1/en unknown
- 1973-02-13 IL IL41522A patent/IL41522A/en unknown
- 1973-02-14 KR KR7300264A patent/KR780000089B1/en not_active Expired
- 1973-02-21 GB GB846873A patent/GB1394409A/en not_active Expired
- 1973-03-02 IE IE339/73A patent/IE37363B1/en unknown
- 1973-04-03 JP JP3749673A patent/JPS5532704B2/ja not_active Expired
- 1973-04-23 PH PH14537*UA patent/PH9390A/en unknown
- 1973-07-15 EG EG277/73A patent/EG11435A/en active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2192820B1 (en) | 1976-07-02 |
| AU471164B2 (en) | 1976-04-08 |
| KR780000089B1 (en) | 1978-04-08 |
| JPS5532704B2 (en) | 1980-08-26 |
| OA04313A (en) | 1980-01-15 |
| CS174865B2 (en) | 1977-04-29 |
| YU36499B (en) | 1984-02-29 |
| EG11435A (en) | 1977-03-31 |
| ES409348A1 (en) | 1975-11-16 |
| BG20347A3 (en) | 1975-11-05 |
| HU167514B (en) | 1975-10-28 |
| MC961A1 (en) | 1973-12-07 |
| AT319932B (en) | 1975-01-10 |
| NL7215710A (en) | 1974-01-22 |
| PL82470B1 (en) | 1975-10-31 |
| PH9390A (en) | 1975-10-22 |
| ZA73537B (en) | 1973-10-31 |
| ZM1773A1 (en) | 1973-10-22 |
| LU66787A1 (en) | 1973-03-19 |
| IE37363L (en) | 1974-01-19 |
| AU5151473A (en) | 1974-08-01 |
| CA976974A (en) | 1975-10-28 |
| JPS4943966A (en) | 1974-04-25 |
| YU301572A (en) | 1982-02-25 |
| JPS4935377A (en) | 1974-04-01 |
| RO62350A (en) | 1977-08-15 |
| GB1394409A (en) | 1975-05-14 |
| CH565149A5 (en) | 1975-08-15 |
| DE2257624A1 (en) | 1974-02-07 |
| AR194145A1 (en) | 1973-06-22 |
| BE793871A (en) | 1973-05-02 |
| IE37363B1 (en) | 1977-07-06 |
| IL41522A0 (en) | 1973-04-30 |
| FR2192820A1 (en) | 1974-02-15 |
| DD102380A5 (en) | 1973-12-12 |
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