IE43001B1 - Process for preparing benzenesulphonamides - Google Patents
Process for preparing benzenesulphonamidesInfo
- Publication number
- IE43001B1 IE43001B1 IE116776A IE116776A IE43001B1 IE 43001 B1 IE43001 B1 IE 43001B1 IE 116776 A IE116776 A IE 116776A IE 116776 A IE116776 A IE 116776A IE 43001 B1 IE43001 B1 IE 43001B1
- Authority
- IE
- Ireland
- Prior art keywords
- methoxy
- pyrrolidinylmethyl
- ethyl
- sulphamoylbenzamide
- preparing
- 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
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)
Abstract
1497005 Process for benzenesulphonamides SOC D'ETUDES SCIENTIFIQUES ET INDUSTRIELLES DE L'ILE-DE-FRANCE 8 June 1976 [11 June 1975] 23696/76 Heading C2C The invention comprises a process for making N - (1 - ethyl - 2 - pyrrolidinomethyl) - 2 - methoxy - 5 - sulphamoylbenzamide (I) by treating (II) with an alkali metal borohydride and a polyvalent metal halide in a solvent.
Description
The invention concerns a new method of preparing N(l-ethyl-2pyrrolIdInylmethyl)-2-methoxy-5-sulphamoylbenzamide, its salts of addition with pharmaceutically acceptable inorganic or organic acids, and quaternary ammonium salts obtained by reacting the benzamide with a quaternizing agent, e.g. an aliphatic or aromatic alkylating agent.
The method of the invention comprises selectively reducing the tertiary amide group in N(l-acetyl“2-pyrroHdinylmethyl)-2-methoxy-5-sulphamoylbenzamide without affecting the secondary amide group, to give N(lethyl-2-pyrrolidinyImethyl)-2-methoxy-5-sulpharaoylbenzaraide.
The benzamide for which the invention discloses a new method of preparation has important pharmacological properties described in French
Patents Nos 4879 M and 5916 M.
The method of the Invention is summarised by the following reaction scheme:
The reduction according to the invention is carried out by means of an alkali metal borohydride and a polyvalent metal halide such as aluminium chloride, gallium chloride or titanium tetrachloride.
The solvents used are solvents capable of dissolving the catalysts 5 used, e.g. Diglyme (diethylene glycol dimethyl ether).
The product can then be converted to an acid-addition or quaternary ammonium salt by reaction with an acid known to be pharmaceutically acceptable or with a suitable quaternizing agent.
The following Example is given to illustrate the invention without 10 imposing any restrictions on it:
N-(l-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-sulphamoylbenzamide
3.55 g of N-(l-acetyl-2-pyrrolidinylmethyl)-2-methoxy-5sulphamoylbenzamide, 35 ml of Diglyme and 0.51 g of sodium borohydride are placed in a 250-ml flask.
The mixture is agitated for 5 minutes at 20°C, then a solution of 0.8 g of aluminium chloride in 10 ml of diglyme is dripped in.
The mixture is heated for 3 hours at 110°C. After cooling, the suspension formed is poured into a solution of 10 ml of hydrochloric acid (d = 1.18) in 30 ml of water. The mixture is brought to the boil for 5 minutes and then cooled. The solvents are evaporated under vacuum, the crystallised residue obtained is dissolved in water and the solution formed is made alkaline by ammonia. When the mixture has been extracted 3 times with 50-ml portions of ethyl acetate and the solvent has been evaporated^ the residue obtained is recrystallised from ethanol.
1.4 g of N-(l-ethyl-2-pyrrolidinylmethyl)-2-methoxy~5-sulphamoylbenzamide is obtained (MP : 178-180°C).
Claims (7)
1. CLAIMS:-. 1 A method of preparing N-(l-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5sulphamoylbenzamide, that comprises selectively reducing the tertiary amide group of N-(l-acetyl-2-pyrrolidinylmethyl)-2~methoxy-5-sulphamoylbenzamide to produce N-(l-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-sulphamoylbenzamide by the action of an alkali metal borohydride and a polyvalent metal halide in a solvent.
2. A method according to claim 1, in which the alkali metal borohydride is sodium borohydride.
3. A method according to claim 1 or 2, in which the polyvalent metal halide is aluminium chloride.
4. A method according to any one of claims 1-3, in which the product is further reacted with a pharmaceutically acceptable inorganic or organic acid to form an acid-addition salt.
5. A method according to any one of claims 1-3, in which the product is further reacted with a quaternizing agent to form a quaternary ammonium salt.
6. A method according to claim 1, substantially as hereinbefore described in the Example.
7. N-(l-ethyl~2-pyrrolidinylmethyl}-2-methoxy-5-sulphaaoylbenzamide, when prepared by a method according to any one of claims 1-6.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7518180A FR2314178A1 (en) | 1975-06-11 | 1975-06-11 | NEW PROCESS FOR THE PREPARATION OF N- (1-ETHYL-2-PYRROLIDYLMETHYL) 2-METHOXY 5-METHOXY 5-SULFAMOYL BENZAMIDE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43001L IE43001L (en) | 1976-12-11 |
| IE43001B1 true IE43001B1 (en) | 1980-12-03 |
Family
ID=9156330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE116776A IE43001B1 (en) | 1975-06-11 | 1976-06-01 | Process for preparing benzenesulphonamides |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5231068A (en) |
| AT (1) | AT349458B (en) |
| CA (1) | CA1064944A (en) |
| DE (1) | DE2623077A1 (en) |
| FI (1) | FI761680A (en) |
| FR (1) | FR2314178A1 (en) |
| GB (1) | GB1497005A (en) |
| IE (1) | IE43001B1 (en) |
| MX (1) | MX3519E (en) |
| PT (1) | PT65165B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1141095B (en) * | 1980-11-27 | 1986-10-01 | Ravizza Spa | RESOLUTION PROCESS OF THE SULPYRID RACEMA |
| EP0091528B1 (en) * | 1982-04-08 | 1986-07-23 | Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France | -n-(1-propyl-2-pyrrolidylmethyl)-2-methoxy-5-sulfamoyl benzamide and its use against some sorts of depression |
| DE4425070A1 (en) * | 1994-07-15 | 1996-01-18 | Degussa | Process for the preparation of optically active l-substituted 2- (aminomethyl) pyrrolidines |
| JP7406897B2 (en) * | 2018-12-07 | 2023-12-28 | キヤノン株式会社 | Conveyance device and article manufacturing method |
-
1975
- 1975-06-11 FR FR7518180A patent/FR2314178A1/en active Granted
-
1976
- 1976-05-22 DE DE19762623077 patent/DE2623077A1/en not_active Withdrawn
- 1976-06-01 AT AT400076A patent/AT349458B/en not_active IP Right Cessation
- 1976-06-01 PT PT6516576A patent/PT65165B/en unknown
- 1976-06-01 IE IE116776A patent/IE43001B1/en unknown
- 1976-06-08 GB GB2369676A patent/GB1497005A/en not_active Expired
- 1976-06-08 JP JP6755176A patent/JPS5231068A/en active Pending
- 1976-06-09 CA CA254,479A patent/CA1064944A/en not_active Expired
- 1976-06-09 MX MX29276U patent/MX3519E/en unknown
- 1976-06-11 FI FI761680A patent/FI761680A/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5231068A (en) | 1977-03-09 |
| PT65165B (en) | 1977-11-17 |
| FR2314178B1 (en) | 1979-04-27 |
| PT65165A (en) | 1976-07-01 |
| AT349458B (en) | 1979-04-10 |
| ATA400076A (en) | 1978-09-15 |
| IE43001L (en) | 1976-12-11 |
| GB1497005A (en) | 1978-01-05 |
| DE2623077A1 (en) | 1976-12-30 |
| FR2314178A1 (en) | 1977-01-07 |
| MX3519E (en) | 1981-01-20 |
| CA1064944A (en) | 1979-10-23 |
| FI761680A (en) | 1976-12-12 |
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