IE52513B1 - Process for the preparation of 4-aminobutyramide - Google Patents
Process for the preparation of 4-aminobutyramideInfo
- Publication number
- IE52513B1 IE52513B1 IE49/82A IE4982A IE52513B1 IE 52513 B1 IE52513 B1 IE 52513B1 IE 49/82 A IE49/82 A IE 49/82A IE 4982 A IE4982 A IE 4982A IE 52513 B1 IE52513 B1 IE 52513B1
- Authority
- IE
- Ireland
- Prior art keywords
- process according
- aminobutyramide
- nitrobutyramide
- hydrogenation
- preparation
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Catalysts (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
1. A process for the preparation of 4-aminobutyramide characterized in that 4-nitrobutyramide is reduced by hydrogenation in the presence of a catalyst.
Description
The present invention relates to a process for the preparation of gabamide.
Various preparations of gabamide, or 4-aminobutyramide, have already been described in the literature; in particular, the article in Angew.
Chem. Int. Ed. 19 (1980), page 627, describes the selective hydrogenation of 3-cyanopropionamide in the presence of hydrogen chloride.
The present invention relates to an economical 10 process which leads to gabamide with a very good yield.
The process of the invention is illustrated in the following scheme: nh4oh/nh4ci NO2-CH2-CH2-CH2-COOAlkyl-^N02-CH2-CH2-CH2-C0NH2 | [hJ/hci NH2-CH2-CH2-CH2-CONH2 The starting compound, namely an alkyl 4-nitrobutanoate, more particularly methyl 4-nitrobutanoate, is described in J. Org. Chem. 1962, 1609.
The first step of the process consists in converting the alkyl 4-nitrobutanoate to 4-nitrobutyramide by any suitable means for converting an ester to an amide, for example by aminolysis, in particular in the presence of ammonia solution and ammonium chloride. 4-Nitrobutyramide is known and has been prepared by a different method, also described in J. Org. Chem. 1962, 1609. An example of aminolysis of a methyl ester is to be found in French Patent No. 2 224 451.
The reduction of 4-nitrobutyramide to 4-aminobutyramide is carried out by hydrogenation in the presence of a catalyst; it can be carried out, in particular, in the presence of an acid, under a pressure ranging, for example, from 1 to 10 bars, and at a temperature ranging from 0 to 50°C.
The hydrogenation catalysts are, for example, platinum oxide (PtOj) or Raney nickel.
The preferred acid is hydrochloric acid.
These mild conditions may be compared with those described in French Patent No. 2 226 388 for the hydrogenation of 6-nitrohexanamide.
The following Example illustrates the invention. 1. 4-NITROBtJTYRAMIDE In a 500 ml Erlenmeyer flask, 15 g (0.102 mol) of methyl 4-nitrobutanoate are introduced into 60 ml of ammonia solution (density: 0.92) and 1.5 g (0.03 mol) of ammonium chloride. The mixture is stirred overnight by means of a magnetic stirrer at the temperature of the laboratory. The solution is concentrated in vacuo at 45-50°C. The residue is taken up in 200 ml of ethyl acetate and the solution is filtered to remove the salts therefrom. A small amount of activated charcoal is added, the mixture is filtered and the solution is concentrated to a third of the initial volume. The product crystallises in the form of white crystals.
Melting point = 89°C (Kofler); 88-89°C (Tottoli: l°C/minute).
Yield: 13.47 g (100%).
The IR and NMR spectra are consistent. 2. 4-AMINOBUTYRAMIDE (HYDROCHLORIDE) 0.25 g (1.9 millimols) of 4-nitrobutyramide, ml of methanol, 5 ml of IN hydrochloric acid and 0.02 g of platinum oxide (PtO2) are introduced into a Parr bomb. The mixture is agitated for 2 hours at 20°C under hydrogen (4 bars). The platinum is filtered off and the solution is concentrated. The residual mass is taken up in 5 ml of ethanol. 20 ml of ethyl acetate are then added to the solution. The crystalline product is filtered off and dried.
Melting point = 139-140°C (Kofler); 138°C (Tottoli: l°C/minute).
Yield: 0.218 g (98%). 53513 The IR and NMR spectra are identical to those of the authentic product.
The process of the invention makes it possible to obtain gabamide with a very good yield and economically, gabamide being a product known for its psychotropic properties and a starting material for syntheses which lead to benzylidene derivatives having very valuable pharmacological properties.
Claims (10)
1. CLAIMSΣΙ. A process for the preparation of 4-aminobutyramide which comprises reducing 4-nitrobutyramide by hydrogenation in the presence of a catalyst. 5
2. A process according to claim 1, in which the catalyst is platinum oxide or Raney nickel.
3. A process according to claim 2, in which the hydrogenation is carried out in the presence of platinum oxide and an acid. 10 4. A process according to claim 3, in which the acid is hydrochloric acid.
4. -nitrobutanoate is converted to 4-nitrobutyramide by 20 aminolysis. 4-nitrobutyramide is obtained from an alkyl 4-nitrobutanoate.
5. A process according to any one of claims 1 to 4 in which the catalytic hydrogenation of 4-nitrobutyramide is carried out under a pressure ranging from 1 to 10 bars and 15 at a temperature ranging from 0 to 50°C.
6. A process according to claim 1, in which the
7. A process according to claim 6, in which an alkyl
8. A process according to claim 7, in which the aminolysis is carried out using ammonia solution and ammonium chloride. 53513
9. A process according to claim 1 for the preparation of 4-aminobutyramide, substantially as hereinbefore described with particular reference to Example 2 of the accompanying Examples.
10. 4-Aminobutyramide whenever prepared by a process 5 claimed in a preceding claim.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8100440A FR2497797A1 (en) | 1981-01-13 | 1981-01-13 | PROCESS FOR THE PREPARATION OF AMINO-4 BUTYRAMIDE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE820049L IE820049L (en) | 1982-07-13 |
| IE52513B1 true IE52513B1 (en) | 1987-11-25 |
Family
ID=9254051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE49/82A IE52513B1 (en) | 1981-01-13 | 1982-01-12 | Process for the preparation of 4-aminobutyramide |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0056343B1 (en) |
| JP (1) | JPS57139046A (en) |
| AT (1) | ATE6933T1 (en) |
| AU (1) | AU7945582A (en) |
| DE (1) | DE3260086D1 (en) |
| DK (1) | DK10082A (en) |
| ES (1) | ES8502080A1 (en) |
| FI (1) | FI820092L (en) |
| FR (1) | FR2497797A1 (en) |
| GR (1) | GR75180B (en) |
| IE (1) | IE52513B1 (en) |
| IL (1) | IL64760A0 (en) |
| NO (1) | NO820073L (en) |
| NZ (1) | NZ199468A (en) |
| PT (1) | PT74274A (en) |
| ZA (1) | ZA82185B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN2012DN02643A (en) * | 2009-10-06 | 2015-09-11 | Bayer Cropscience Ag |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1225419A (en) * | 1958-07-29 | 1960-06-30 | Montedison Spa | Process for the preparation of omega-aminocaprylic acid amide and products obtained by this process |
| DE2316459C2 (en) * | 1973-04-03 | 1982-06-24 | Hoechst Ag, 6000 Frankfurt | Process for the preparation of 1-nitrobenzene-2-carboxylic acid alkyl ester-5-carboxamides |
| DE2319360A1 (en) * | 1973-04-17 | 1974-11-07 | Basf Ag | PROCESS FOR THE PRODUCTION OF EPSILONAMINOCAPRONIC ACID AMIDE |
-
1981
- 1981-01-13 FR FR8100440A patent/FR2497797A1/en active Granted
-
1982
- 1982-01-07 EP EP82400013A patent/EP0056343B1/en not_active Expired
- 1982-01-07 DE DE8282400013T patent/DE3260086D1/en not_active Expired
- 1982-01-07 AT AT82400013T patent/ATE6933T1/en not_active IP Right Cessation
- 1982-01-12 ZA ZA82185A patent/ZA82185B/en unknown
- 1982-01-12 GR GR66987A patent/GR75180B/el unknown
- 1982-01-12 ES ES508656A patent/ES8502080A1/en not_active Expired
- 1982-01-12 AU AU79455/82A patent/AU7945582A/en not_active Abandoned
- 1982-01-12 DK DK10082A patent/DK10082A/en not_active Application Discontinuation
- 1982-01-12 IE IE49/82A patent/IE52513B1/en unknown
- 1982-01-12 IL IL64760A patent/IL64760A0/en unknown
- 1982-01-12 NO NO820073A patent/NO820073L/en unknown
- 1982-01-12 NZ NZ199468A patent/NZ199468A/en unknown
- 1982-01-12 JP JP57003985A patent/JPS57139046A/en active Pending
- 1982-01-12 PT PT74274A patent/PT74274A/en unknown
- 1982-01-12 FI FI820092A patent/FI820092L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ199468A (en) | 1984-05-31 |
| ATE6933T1 (en) | 1984-04-15 |
| FR2497797B1 (en) | 1983-12-23 |
| FI820092L (en) | 1982-07-14 |
| AU7945582A (en) | 1982-07-22 |
| IL64760A0 (en) | 1982-03-31 |
| ES508656A0 (en) | 1984-12-01 |
| FR2497797A1 (en) | 1982-07-16 |
| JPS57139046A (en) | 1982-08-27 |
| DE3260086D1 (en) | 1984-05-10 |
| EP0056343B1 (en) | 1984-04-04 |
| IE820049L (en) | 1982-07-13 |
| DK10082A (en) | 1982-07-14 |
| NO820073L (en) | 1982-07-14 |
| EP0056343A1 (en) | 1982-07-21 |
| ZA82185B (en) | 1983-01-26 |
| PT74274A (en) | 1982-02-01 |
| GR75180B (en) | 1984-07-13 |
| ES8502080A1 (en) | 1984-12-01 |
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