GB595540A - 1:4-diamino-2-butines - Google Patents
1:4-diamino-2-butinesInfo
- Publication number
- GB595540A GB595540A GB1728745A GB1728745A GB595540A GB 595540 A GB595540 A GB 595540A GB 1728745 A GB1728745 A GB 1728745A GB 1728745 A GB1728745 A GB 1728745A GB 595540 A GB595540 A GB 595540A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butine
- dichloro
- prepared
- refluxing
- butines
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 6
- 238000010992 reflux Methods 0.000 abstract 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 3
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-Butylamine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-Methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic Effects 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1 : 4-Diamino-2-butines of the general formula RR1NCH2C=CCH2NR1R, where R and R1 need not be the same and represent hydrogen, hydrocarbon radicals or together form an alkylene chain, are prepared by reacting one molecular proportion of 1 : 4-dichloro-, 1 : 4-dibromo- or 1 : 4-diiodo-2-butines with two molecular proportions of a compound of the general formula RR1NH, where R and R1 have the significance indicated above, with or without heating and a water or organic liquid medium, e.g. benzene, toluene, n-butanol, ligroin or ether may be used. The products may be reduced to give 1 : 4-diaminobutanes. In examples: (1) and (2) 1 : 4-diamino- and 1 : 4-dimethylamino-2-butines are prepared by reacting 1 : 4-dichloro-2-butine with aqueous ammonia and methylamine respectively; (3) and (4) 1 : 4-dibutylamino- and 1 : 4-dicyclohexylamino-2-butine are prepared by refluxing 1 : 4-dichloro-2-butine dissolved in benzene with n-butylamine and cyclohexylamine respectively; (5) 1 : 4-dichloro-2-butine, aniline and n-butanol are refluxed to yield 1 : 4-dianilino-2-butine which may be converted to diacetanilido-2-butine; (6), (7) and (8) 1 : 4-dipiperidino-2-butine is prepared by refluxing piperidine, benzene and 1 : 4-dichloro-, 1 : 4-dibromo- or 1 : 4-diiodo-2-butine; (9) 1 : 4-bis-(dimethylamino)-2-butine is prepared by refluxing 1 : 4-dichloro-2-butine and aqueous dimethylamine; (10) 1 : 4-di-(methylanilino)-2-butine is prepared by refluxing methylaniline, n-butanol and 1 : 4-dichloro-2-butine 1 : 4-Diiodo-2-butine is prepared by reacting 1 : 4-dibromo- or 1 : 4-dichloro-2-butine, which may be prepared as described in Specification 595,539 with alcoholic potassium iodide.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB595540A true GB595540A (en) | 1947-12-08 |
Family
ID=1732983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1728745A Expired GB595540A (en) | 1945-07-06 | 1:4-diamino-2-butines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB595540A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2766285A (en) * | 1952-10-20 | 1956-10-09 | Lilly Co Eli | Substituted aminopropynes and process for their preparation |
| DE1206426B (en) * | 1960-02-29 | 1965-12-09 | Lilly Co Eli | Process for the preparation of an alkynamine |
| DE1210806B (en) * | 1960-02-29 | 1966-02-17 | Lilly Co Eli | Process for the preparation of secondary alkyl or alkyleneamines or their non-toxic salts |
| DE1265742B (en) * | 1965-11-25 | 1968-04-11 | Hoechst Ag | Process for the preparation of 1,4-bis- (monoalkylamino) -trans-butenen- (2) |
| US5151459A (en) * | 1991-05-16 | 1992-09-29 | Ciba-Geigy Corporation | Substituted 1,4-diamino-2-butyne or propargylamine as stabilizers for compositions |
-
1945
- 1945-07-06 GB GB1728745A patent/GB595540A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2766285A (en) * | 1952-10-20 | 1956-10-09 | Lilly Co Eli | Substituted aminopropynes and process for their preparation |
| DE1206426B (en) * | 1960-02-29 | 1965-12-09 | Lilly Co Eli | Process for the preparation of an alkynamine |
| DE1210806B (en) * | 1960-02-29 | 1966-02-17 | Lilly Co Eli | Process for the preparation of secondary alkyl or alkyleneamines or their non-toxic salts |
| DE1265742B (en) * | 1965-11-25 | 1968-04-11 | Hoechst Ag | Process for the preparation of 1,4-bis- (monoalkylamino) -trans-butenen- (2) |
| US5151459A (en) * | 1991-05-16 | 1992-09-29 | Ciba-Geigy Corporation | Substituted 1,4-diamino-2-butyne or propargylamine as stabilizers for compositions |
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