NO820073L - PROCEDURE FOR THE PREPARATION OF 4-AMINOBUTYRAMIDES - Google Patents
PROCEDURE FOR THE PREPARATION OF 4-AMINOBUTYRAMIDESInfo
- Publication number
- NO820073L NO820073L NO820073A NO820073A NO820073L NO 820073 L NO820073 L NO 820073L NO 820073 A NO820073 A NO 820073A NO 820073 A NO820073 A NO 820073A NO 820073 L NO820073 L NO 820073L
- Authority
- NO
- Norway
- Prior art keywords
- stated
- nitro
- butyramide
- preparation
- carried out
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- CUSYXOQIPLRISK-UHFFFAOYSA-N 4-nitrobutanamide Chemical compound NC(=O)CCC[N+]([O-])=O CUSYXOQIPLRISK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 6
- WCVPFJVXEXJFLB-UHFFFAOYSA-N 4-aminobutanamide Chemical compound NCCCC(N)=O WCVPFJVXEXJFLB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 4
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 4
- 238000007098 aminolysis reaction Methods 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UBSPKGKFFQKZJB-UHFFFAOYSA-N methyl 4-nitrobutanoate Chemical compound COC(=O)CCC[N+]([O-])=O UBSPKGKFFQKZJB-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YKAWOJYVXDCFDP-UHFFFAOYSA-N 3-cyanopropanamide Chemical compound NC(=O)CCC#N YKAWOJYVXDCFDP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- -1 by aminolysis Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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
Abstract
Description
Foreliggende oppfinnelse vedrører en fremgangsmåte for fremstilling av 4-butyramid og det særegne ved fremgangsmåten i' henhold til oppfinnelsen er at man reduserer 4-nitrobutyramid. The present invention relates to a method for the production of 4-butyramide and the distinctive feature of the method according to the invention is that 4-nitrobutyramide is reduced.
Disse og andre trekk ved oppfinnelsen fremgår av patent-kravene. These and other features of the invention appear in the patent claims.
I litteraturen er tidligere beskrevet forskjellige metoder for fremstilling av 4-amino-butyramid eller såkalt "gabamid", se spesielt artikkelen i Angew. Chem. Int. Ed. 19 (1980), side 627 som beskriver selektiv hydrogenering av 3-cyano-propionamid i nærvær av hydro-genklorid. Various methods for the production of 4-amino-butyramide or so-called "gabamid" have previously been described in the literature, see in particular the article in Angew. Chem. Int Ed. 19 (1980), page 627 which describes the selective hydrogenation of 3-cyano-propionamide in the presence of hydrogen chloride.
Den foreliggende oppfinnelse vedrører en overraskende enkel og lønnsom fremgangsmåte som fører til gabamid med meget godt utbytte og fremgangsmåten i henhold til oppfinnelsen kan representeres ved hjelp av følgende reak-sjonsskj erna The present invention relates to a surprisingly simple and profitable method which leads to gabamide with a very good yield and the method according to the invention can be represented by means of the following reaction core
Utgangsforbindelsen, nemlig alkyl-4-nitro-butanoat og mer spesielt metyl-4-nitrobutanoat, er beskrevet i litteraturen, se J. Org- Chem, 1962,! 1609. The starting compound, namely alkyl-4-nitro-butanoate and more particularly methyl-4-nitrobutanoate, is described in the literature, see J. Org-Chem, 1962,! 1609.
Det første trinn i fremgangsmåten består i å omdanne alkyl-4-nitro-butanoatet til 4-nitro-butyramid ved hjelp av passende midler for omdannelse av en ester til et amid, f.eks. ved aminolyse, spesielt i nærvær av ammoniakk og ammoniumklorid. 4-nitrobutyramid er kjent og er blitt fremstilt ved hjelp av en forskjellig metode likeledes beskrevet i J. Org. Chem., 1962, 1609. The first step in the process consists in converting the alkyl-4-nitro-butanoate to 4-nitro-butyramide by means of suitable means for converting an ester to an amide, e.g. by aminolysis, especially in the presence of ammonia and ammonium chloride. 4-nitrobutyramide is known and has been prepared using a different method likewise described in J. Org. Chem., 1962, 1609.
Reduksjonen av 4-nitro-butyramid til 4-amino-butyramid gjennomføres ved hjelp av hvilke som helst passende midler for reduksjon av nitrogruppen og kan spesielt gjennomføres ved hydrogenering i nærvær av en kata- The reduction of 4-nitro-butyramide to 4-amino-butyramide is carried out by any suitable means for the reduction of the nitro group and can in particular be carried out by hydrogenation in the presence of a cata-
lysator og en syre, under et trykk på fra 1 til 10 bar og en temperatur fra 0 til 50°C. lysator and an acid, under a pressure of from 1 to 10 bar and a temperature of from 0 to 50°C.
Hydrogeneringskatalysatorene er f.eks. platinaoksyd Pt02eller Raney-nikkel. The hydrogenation catalysts are e.g. platinum oxide PtO 2 or Raney nickel.
Den syre som foretrekkes er saltsyre. The preferred acid is hydrochloric acid.
Følgende eksempler illustrerer oppfinnelsen. The following examples illustrate the invention.
EKSEMPEL 1 EXAMPLE 1
A. 4-nitro-butyramid A. 4-nitro-butyramide
I en 500 ml erlenmeyer-kolbe innføres 15 g (0,102 m) metyl-4-nitro-butanoat i 60 ml ammoniakk (densitet 0,92) og 1,5 g (0,03 m) ammoniumklorid. Det omrøres magnetisk over natten ved romtemperaturen. Oppløsningen inndampes under vakuum ved 45 til 50°C. Resten opptas i 200 ml etylacetat og oppløsningen filtreres for fjernelse av salter. Litt aktivkarbon tilsettes, og oppløsningen filtreres og inndampes til 1/3 av det initiale volum. Produktet krystalli,-serer i form av hvite krystaller. Into a 500 ml Erlenmeyer flask, introduce 15 g (0.102 m) of methyl 4-nitro-butanoate in 60 ml of ammonia (density 0.92) and 1.5 g (0.03 m) of ammonium chloride. It is magnetically stirred overnight at room temperature. The solution is evaporated under vacuum at 45 to 50°C. The residue is taken up in 200 ml of ethyl acetate and the solution is filtered to remove salts. A little activated carbon is added, and the solution is filtered and evaporated to 1/3 of the initial volume. The product crystallizes in the form of white crystals.
Smeltepunkt = 89°C (Kofler)/88-89°C (Tottoli: 1°C). Melting point = 89°C (Kofler)/88-89°C (Tottoli: 1°C).
Utbytte: 13,47 g (100%). Yield: 13.47 g (100%).
Spektra IR og RMN bekreftes. IR and NMR spectra are confirmed.
B. 4- amino- butyramid ( hydroklorid) B. 4-amino-butyramide (hydrochloride)
I en Parr-bombe innføres 0,25 g (1,9 m mol) 4-nitrobutyr- In a Parr bomb, 0.25 g (1.9 m mol) of 4-nitrobutyr-
amid, 20 ml metanol, 5 ml 1 N saltsyre og 0,02 Pt02. Det omrøres i 2 timer ved 20°C under hydrogen (4 bar) platina-oksydet frafiltreres og oppløsningen inndampes og resten amide, 20 mL methanol, 5 mL 1 N hydrochloric acid, and 0.02 PtO 2 . It is stirred for 2 hours at 20°C under hydrogen (4 bar), the platinum oxide is filtered off and the solution is evaporated and the residue
opptas i 5 ml etanol. Oppløsningen tilsettes så 20 ml etylacetat og det krystalliserte produkt frafiltreres og tørkes. taken up in 5 ml of ethanol. The solution is then added with 20 ml of ethyl acetate and the crystallized product is filtered off and dried.
Smeltepunkt = 139 - 140°C (Kofler); 138°C (Tottoli: l°C/min.). Melting point = 139 - 140°C (Kofler); 138°C (Tottoli: 1°C/min.).
Utbytte: 0,218 g (98%) Yield: 0.218 g (98%)
Spektra IR og RMN er identiske med en autentisk produkt-prøve. The IR and RMN spectra are identical to an authentic product sample.
Fremgangsmåten i henhold til oppfinnelsen tillater at The method according to the invention allows that
man med meget godt utbytte og på økonomisk måte kan fremstille gabamid som er et produkt kjent for sine psykotrope egenskaper og utgangsmaterial for syntese som fører til benzyliden-derivater med verdifulle farmakologiske egenskaper. gabamide, which is a product known for its psychotropic properties and starting material for synthesis that leads to benzylidene derivatives with valuable pharmacological properties, can be produced with very good yield and economically.
Claims (8)
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 (1)
| Publication Number | Publication Date |
|---|---|
| NO820073L true NO820073L (en) | 1982-07-14 |
Family
ID=9254051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO820073A NO820073L (en) | 1981-01-13 | 1982-01-12 | PROCEDURE FOR THE PREPARATION OF 4-AMINOBUTYRAMIDES |
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) | ES508656A0 (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 |
|---|---|---|---|---|
| BR112012006839A2 (en) * | 2009-10-06 | 2016-06-07 | Bayer Cropscience Ag | Method for the production of 2,2-difluoroethylamine by hydrogenation of 1-1-difluor-2-nitroethane |
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 IL IL64760A patent/IL64760A0/en unknown
- 1982-01-12 NO NO820073A patent/NO820073L/en unknown
- 1982-01-12 AU AU79455/82A patent/AU7945582A/en not_active Abandoned
- 1982-01-12 ZA ZA82185A patent/ZA82185B/en unknown
- 1982-01-12 ES ES508656A patent/ES508656A0/en active Granted
- 1982-01-12 JP JP57003985A patent/JPS57139046A/en active Pending
- 1982-01-12 NZ NZ199468A patent/NZ199468A/en unknown
- 1982-01-12 IE IE49/82A patent/IE52513B1/en unknown
- 1982-01-12 GR GR66987A patent/GR75180B/el unknown
- 1982-01-12 PT PT74274A patent/PT74274A/en unknown
- 1982-01-12 DK DK10082A patent/DK10082A/en not_active Application Discontinuation
- 1982-01-12 FI FI820092A patent/FI820092L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU7945582A (en) | 1982-07-22 |
| ZA82185B (en) | 1983-01-26 |
| NZ199468A (en) | 1984-05-31 |
| JPS57139046A (en) | 1982-08-27 |
| ATE6933T1 (en) | 1984-04-15 |
| FR2497797A1 (en) | 1982-07-16 |
| IE820049L (en) | 1982-07-13 |
| ES8502080A1 (en) | 1984-12-01 |
| FR2497797B1 (en) | 1983-12-23 |
| EP0056343A1 (en) | 1982-07-21 |
| FI820092L (en) | 1982-07-14 |
| DE3260086D1 (en) | 1984-05-10 |
| GR75180B (en) | 1984-07-13 |
| IE52513B1 (en) | 1987-11-25 |
| EP0056343B1 (en) | 1984-04-04 |
| PT74274A (en) | 1982-02-01 |
| DK10082A (en) | 1982-07-14 |
| ES508656A0 (en) | 1984-12-01 |
| IL64760A0 (en) | 1982-03-31 |
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