US471520A - H xtttvtyti - Google Patents
H xtttvtyti Download PDFInfo
- Publication number
- US471520A US471520A US471520DA US471520A US 471520 A US471520 A US 471520A US 471520D A US471520D A US 471520DA US 471520 A US471520 A US 471520A
- Authority
- US
- United States
- Prior art keywords
- piperazin
- september
- solution
- spermin
- dated
- 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 - Lifetime
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 22
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229940063675 spermine Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- -1 piperazin hydrocarbon compounds Chemical class 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- SMSNTRICQUSSBP-UHFFFAOYSA-N 2,2-dinitroso-1,4-diphenylpiperazine Chemical compound N(=O)C1(N(CCN(C1)C1=CC=CC=C1)C1=CC=CC=C1)N=O SMSNTRICQUSSBP-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 241000219991 Lythraceae Species 0.000 description 2
- 235000014360 Punica granatum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 230000002238 attenuated effect Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 235000007715 potassium iodide Nutrition 0.000 description 2
- 229960004839 potassium iodide Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NQQWFVUVBGSGQN-UHFFFAOYSA-N phosphoric acid;piperazine Chemical compound OP(O)(O)=O.C1CNCCN1 NQQWFVUVBGSGQN-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KOECRLKKXSXCPB-UHFFFAOYSA-K triiodobismuthane Chemical compound I[Bi](I)I KOECRLKKXSXCPB-UHFFFAOYSA-K 0.000 description 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
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
Definitions
- VVILHELM MAJERT OF BERLIN, GERMANY, ASSIGNOR TO THE OHEMISCHE- FABRIK AUEACTIEN, (VORMALS E. SOHERING,) OF SAME PLACE.
- the invention consists in a novel process or mode of obtaining pure piperazin having all the properties of pure spermin, and therefore better adaptedfor therapeutic uses than o spermin, which has not heretofore been obtained in achemically-pure state.
- Spermin is a base he discovered in human and animal sperm, and corresponds to the empirical formula C,H N. 3 5 Ladenburg (see Berichte de'r Manual Chemischen Gesellschafif, Vol. 21, p. 758) obtained by heating to a rather high degree hydrochloride of ethylenediamine obtained a base that not only has the same composition as 0 spermin, but also its chemical properties, and he concluded that spermin and its base were simply ethylenediamine which in an aqueous solution should be readily condensible to the piperazin,
- piperazin hydrocar- 6o bon compounds Any of the following piperazin hydrocar- 6o bon compounds may be used, as diphenyl, di-
- the said piperazin hydrocarbon compounds containing in each aromatic nucleus at least one, in general therefore at least two, nitro or nitroso groups or two atoms of a haloid thereofsuch as chlorine, bromine, or iodine-in the ortho or para position relatively to the nitrogen contained in said compounds.
- dinitrosodiethylenediphenyldiamine (dinitrosodiphenylpiperazin) does not undergo any changes when treated with boiling soda-lye. According to my invention and discovery, this is not the case, as dinitrosodiphenylpiperazin, when treated with an alkali or an al- 8o kaline earth, or both, is split up into one molecule of piperaziniand two molecules of nitrosophenol.
- My novel process may therefore be carried out as follows: by combining one part, by Weight, of any of the piperazin hydrocarbon compounds hereinafter named with from two to four parts, by weight, of a soda or potash lye containing about twentyfive per cent. of the alkali. The mixture is then distilled, the piperazin passing over with the aqueous 'vapors,hydrochloric or other suitable acidsuch as phosphoric or sulphuric acid-being added to the products of distillation to form salts, which are then crystallized out by evaporation.
- a solution of an alkaline earth may be usedin the treatmentofthe hydrocarbon compounds of piperazin, or a solution of an alkali and an the properties of spermin or ethylenimine, is
- the free base has the characteristic smell of sperm, is readily soluble in water but not so readily in soda-lye, and crystallizes out of an aqueous solution in the form of square tablets, that glitter like glass, while the hydrochloride crystallizes out of an alcoholic solution in the form of branched spear-like crystals that contain water of crys talliz-a-tion.
- the gold salt crystallizes into yellow glittering foliated crystals, while the base, when treated with picric acid, forms a yellow precipitate or deposit.
- piperazin hydrocarbon compounds which maybe used in my process: Dinitro, dinitroso, trinitro, tetranitro, pentanitro, hexanitro, dichlorine, trichlorine, tetrachlorine, pentachlorine, hexachlorine, dibromine, tribromine, tetrabromine, pentabromine,hexabromine, di-iodine, tri-iodine, tetraiodine, penta-iodine, liexa-iodine, diphenyl,
- the spermine obtained'by him has the following chemical formula: O H N; while piperazin has the for-' I mula G H N a duplication of the Schreiner formula, the percentagesof the compound bemg the same.
- the difference between spermine as obtained by Schreiner and piperazin as obtained by the process described are fully set forth in the report of the German Chemi cal Society (Deutsche Chemissche Gesellsc'hafi) of 1891, first half year, page 241, &c., of which the following are the most salient: Spermine has more of the odor of trimethylamine than piperazin.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
UNITED TATES- PATENT OFFICE,
VVILHELM MAJERT, OF BERLIN, GERMANY, ASSIGNOR TO THE OHEMISCHE- FABRIK AUEACTIEN, (VORMALS E. SOHERING,) OF SAME PLACE.
PROCESS OF MAKING PIPERAZIN.
SPECIFICATION forming part of Letters Patent N 0. 471,520, dated March 22, 1892.
Application fil d November 18, 1890. Serial No. 371,356. (No specimens.) Patentedin Germany September 14, 1890, No. 60,545: in Belgium September 2 1890, N- 92,l45 in France September 29, 1890, No. 208,521: in England September 1 1 15,404; in Norway September 29, 1890, No. 1,910; in Sweden September 29, 1890,].1'0. 2,969; in Italy September 30,1890, XXIV, 28,893, and LV, 4,82 in Luxembnrg September 80, 1890, No. 1,355; in Spain November 14, 1890, No.11,280, and in Denmark March 25, 1891.
To all whom it may concern:
Be it known that I, WILHELM MAJERT, doctor of philosophy and chemist, a subject of the King of Prussia, residing at 10 Madaistr.,
5 in Berlin, Prussia, German Empire, have invented certain new and useful Improvements in the Manufacture of Spermine, (spermin,) (for which Letters Patent have been granted in Belgium, No. 92,145, dated September 29,
1890; in Denmark, dated March 25, 1891; in France, No. 208,521, dated September 29, 1890; in Germany, No. 60,545, dated September. 14,, 1890; in Great Britain, N 0. 15,404, dated September 29, 1890; in Italy, Vol. XXIV, No. 28,393, and Vol. LV, No. 482, dated September 30, 1890; in Luxemburg, No. 1,355, dated September 30, 1890; in Norway, No. 1,910, dated September 29, 1890; in Spain, No. 11,280, dated November 14, 1890, and in Swe- 2o den No. 2,969, dated September 29, 1890;) and I do hereby declare the following to be a full, clear, and exact description of the invention, such as will enable others skilled in the art to which it appertains to make and use the same.
The invention consists in a novel process or mode of obtaining pure piperazin having all the properties of pure spermin, and therefore better adaptedfor therapeutic uses than o spermin, which has not heretofore been obtained in achemically-pure state.
Spermin,as definedbySchneider, is a base he discovered in human and animal sperm, and corresponds to the empirical formula C,H N. 3 5 Ladenburg (see Berichte de'r Deutsche Chemischen Gesellschafif, Vol. 21, p. 758) obtained by heating to a rather high degree hydrochloride of ethylenediamine obtained a base that not only has the same composition as 0 spermin, but also its chemical properties, and he concluded that spermin and its base were simply ethylenediamine which in an aqueous solution should be readily condensible to the piperazin,
According to my invention, I find the above formula to correspond with that of piperazin, and a substantially similar chemical .can be obtained in a chemically-pure state or substantially so by means of a hydrocarbon compound of piperazin containing at least two aromatic hydrocarbon groups. I
Any of the following piperazin hydrocar- 6o bon compounds may be used, as diphenyl, di-
methyl, ditolyl,dixylyl, dimesityl, dipseudocumyl, or dinaphthylpiperazin, which yields the pure piperazin by treatment with an alkali or an alkaline earth, or both, the said piperazin hydrocarbon compounds containing in each aromatic nucleus at least one, in general therefore at least two, nitro or nitroso groups or two atoms of a haloid thereofsuch as chlorine, bromine, or iodine-in the ortho or para position relatively to the nitrogen contained in said compounds.
Morley (see Bem'chte tler Dewfsche Chemischen Gesellschaft, Vol. 12, p. 1795) states that dinitrosodiethylenediphenyldiamine (dinitrosodiphenylpiperazin) does not undergo any changes when treated with boiling soda-lye. According to my invention and discovery, this is not the case, as dinitrosodiphenylpiperazin, when treated with an alkali or an al- 8o kaline earth, or both, is split up into one molecule of piperaziniand two molecules of nitrosophenol. My novel process may therefore be carried out as follows: by combining one part, by Weight, of any of the piperazin hydrocarbon compounds hereinafter named with from two to four parts, by weight, of a soda or potash lye containing about twentyfive per cent. of the alkali. The mixture is then distilled, the piperazin passing over with the aqueous 'vapors,hydrochloric or other suitable acidsuch as phosphoric or sulphuric acid-being added to the products of distillation to form salts, which are then crystallized out by evaporation. Instead of 5 the solution of an alkali referred to above a solution of an alkaline earth may be usedin the treatmentofthe hydrocarbon compounds of piperazin, or a solution of an alkali and an the properties of spermin or ethylenimine, is
substantially chemically pure, and consequently well adapted for therapeutic purposes. The free base has the characteristic smell of sperm, is readily soluble in water but not so readily in soda-lye, and crystallizes out of an aqueous solution in the form of square tablets, that glitter like glass, while the hydrochloride crystallizes out of an alcoholic solution in the form of branched spear-like crystals that contain water of crys talliz-a-tion. \Vhen an acid solution of the base, even a very weak solution, is treated with potassium iodide and bismuth, a precipitate or deposit of a pomegranate color is obtained, which under the microscope shows afoliated form. The gold=salt crystallizes into yellow glittering foliated crystals, while the base, when treated with picric acid, forms a yellow precipitate or deposit.
Thefollowingare the piperazin hydrocarbon compounds which maybe used in my process: Dinitro, dinitroso, trinitro, tetranitro, pentanitro, hexanitro, dichlorine, trichlorine, tetrachlorine, pentachlorine, hexachlorine, dibromine, tribromine, tetrabromine, pentabromine,hexabromine, di-iodine, tri-iodine, tetraiodine, penta-iodine, liexa-iodine, diphenyl,
ditolyl, dixylyl, dimesityl, dipseudocumyl, di-
naphtyl, piperazin.
According to Schreiner the spermine obtained'by him has the following chemical formula: O H N; while piperazin has the for-' I mula G H N a duplication of the Schreiner formula, the percentagesof the compound bemg the same. The difference between spermine as obtained by Schreiner and piperazin as obtained by the process described are fully set forth in the report of the German Chemi cal Society (Deutsche Chemissche Gesellsc'hafi) of 1891, first half year, page 241, &c., of which the following are the most salient: Spermine has more of the odor of trimethylamine than piperazin. With potassium-iodide and bismuth-iodide in a weak solution of hydrochloric acid an orange-floccular crystalline precipitate is obtained, which under the microscope shows long points in soft featherlike groups. Pi-perazin, on the contrary, yields a heavy precipitate of a pomegranate red, and shows under the microscope rectangular elongated tablets that can be'obtained from a solution not too attenuated, while from an attenuated solution parallel bars grouped in the form of stars are obtained. The phosphate of spermine crystallizes out of water in a pyramidal form with rounded point that collect into ornamental rosettes. The piperazin phosphate, on the contrary, crystallizes out of water in flat rectangular tablets, the corners of which are often blunted diagonally.
Having thus described my invention, the following is what I claim as new therein and desire to secure by Letters Patent:
'1. The process of obtaining piperazin from its compounds, which consists in isolating the piperazin in the compound by means of an alkaline solution and separating the piperazin,'as set forth.
2. The process of obtaining piperazin from its compounds, which consists in isolating the piperazin in a hydrocarbon compound thereof containing relatively to the nitrogen therein two or more aromatic-hydrocarbon groups holding in each nucleus one or more nitroor nitroso groups or an atom or atoms of a haloid thereof in the ortho or para position by means of an alkaline solution, and separating the piperazin, as set forth.
3. The process of obtaining piperazin, which consists in isolating the piperazin in a compound thereof by means of an alkaline solu tion, distilling off the piperazin into a suitable acid to form salts, and crystallizing out the salts, asset forth.
In testimony whereof I affix my signature in presence of two witnesses.
WILHELM MAJERT. \Vitnesses:
CARLFEHLERT, ADOLF DEMELIUS.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US471520A true US471520A (en) | 1892-03-22 |
Family
ID=2540379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US471520D Expired - Lifetime US471520A (en) | H xtttvtyti |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US471520A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2553696A (en) * | 1944-01-12 | 1951-05-22 | Union Carbide & Carbon Corp | Method for making water-soluble polymers of lower alkylene imines |
-
0
- US US471520D patent/US471520A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2553696A (en) * | 1944-01-12 | 1951-05-22 | Union Carbide & Carbon Corp | Method for making water-soluble polymers of lower alkylene imines |
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