US1894375A - Basic product and process of making it - Google Patents
Basic product and process of making it Download PDFInfo
- Publication number
- US1894375A US1894375A US1894375DA US1894375A US 1894375 A US1894375 A US 1894375A US 1894375D A US1894375D A US 1894375DA US 1894375 A US1894375 A US 1894375A
- Authority
- US
- United States
- Prior art keywords
- stands
- making
- para
- aliphatic
- acetone
- 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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- 238000000034 method Methods 0.000 title description 16
- 125000001931 aliphatic group Chemical group 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 24
- 125000004432 carbon atoms Chemical group C* 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- 230000001225 therapeutic Effects 0.000 description 8
- 241001325354 Lamiinae Species 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 6
- 125000001302 tertiary amino group Chemical group 0.000 description 6
- ODUCDPQEXGNKDN-UHFFFAOYSA-N Nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- -1 aromatic primary Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-Aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- URWNKCXOKFOPAI-UHFFFAOYSA-N 4-N-[2-(diethylamino)ethyl]-4-N-ethylbenzene-1,4-diamine Chemical compound CCN(CC)CCN(CC)C1=CC=C(N)C=C1 URWNKCXOKFOPAI-UHFFFAOYSA-N 0.000 description 2
- QPLDIIWHNWRNCC-UHFFFAOYSA-N 4-N-[2-(diethylamino)ethyl]-4-N-methylbenzene-1,4-diamine Chemical compound CCN(CC)CCN(C)C1=CC=C(N)C=C1 QPLDIIWHNWRNCC-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- 235000017284 Pometia pinnata Nutrition 0.000 description 2
- 240000009305 Pometia pinnata Species 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
Definitions
- the present invention relates to basic products and process of making them, partlcular- 1y to compounds of the following general formula:
- R stands for an aliphatic hydrocarbon residue containing at least ten carbon atoms
- R stands for O or NH
- R stands for an aliphatic residue with a tertiary am no group or for anamino group which contains at least an aliphatic residue with a tertiary nitrogen atom.
- imino ethers of higher fatty acids or the acids from which these imino ethers are derived, or the esters, chlorides and amides thereof are condensed with aromatic primary or secondary amines, containing a basic side chain with tertiary nitrogen, for instance with para-,B-diethylamino-ethoxyaniline, or with para-aminobenzoyl-diethylamino ethanol or with methyldiethylaminoethyl-paraphenylene-diamine or with ethyldiethylaminoethyl-para-phenylenediamine.
- the process may also be carried out by condensing the said acids and acid derivatives with aromatic primary or secondary amines with no basic side chain'and subsequently introducing a basic side chain into the products thus obtained.
- the product has the following formula:
- the product has the following formula:
- the product has the following formula:
- the product has the following fomnula:
- the product has the following formula:
- R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms
- R stands for a radical of the group consisting of OH, OCH, OC2H OGH2G Hg, C1, NH and R stands for O or NH, to act upon an aromatic polyamino compound of the following general formula:
- R stands for an aliphatic residue with a tertiary amino group or for an amino group which has at least one aliphatic residue containing a tertiary nitrogen.
- R stands for an aliphatic hydrocarbon residue with at least 10 carbon atoms, to act upon an aromatic polyamino compound of the following general formula:
- R stands for an aliphatic residue with a tertiary amino group or for an' amino group which has at least one aliphatic residue containing a tertiary nitrogen.
- R stands for an aliphatic hydrocarbon resldue containing at least 10 carbon atoms, to act upon a compound of the general formula:
- R stands for hydrogen, an alkyl or an aralkyl and R stands for an aliphatic residue containing a tertiary nitrogen atom.
- R stands for an aliphatic hydrocar
- R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms
- R stands for O or NH
- R stands for an aliphatic residue with a tertiary amino group or for an amino group which contains at least an aliphatic residue with a tertiary nitrogen atom, said products possessing valuable therapeutic and technical properties.
- R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms
- R stands for hydrogen or alkyl
- R stands for an aliphatic residue with a tertiary nitrogen
- R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms, said products possessing valuable therapeutical and technical properties.
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Jan. 17, 1933 UNITED STATES PATENT OFFICE ROBERT KNOLL, OF HORNAU IN TAUN'U'S, GERMANY, ASSIGNOR, BY MESNE ASSIGN- MENTS, TO WINTHROP CHEMICAL COMPANY, INC, OF NEW YORK, N. Y., A. CORPORA- TION OF NEW YORK BLASIC PRODUCT AND PROCESS OF MAKING IT No Drawing. Application filed July 30, 1929, Serial No. 382,290, and in Germany August 13, 1928.
The present invention relates to basic products and process of making them, partlcular- 1y to compounds of the following general formula:
wherein R stands for an aliphatic hydrocarbon residue containing at least ten carbon atoms, R stands for O or NH and R stands for an aliphatic residue with a tertiary am no group or for anamino group which contains at least an aliphatic residue with a tertiary nitrogen atom.
These compounds are suitable for therapeutical and technical purposes and are obtained if imino ethers of higher fatty acids or the acids from which these imino ethers are derived, or the esters, chlorides and amides thereof, are condensed with aromatic primary or secondary amines, containing a basic side chain with tertiary nitrogen, for instance with para-,B-diethylamino-ethoxyaniline, or with para-aminobenzoyl-diethylamino ethanol or with methyldiethylaminoethyl-paraphenylene-diamine or with ethyldiethylaminoethyl-para-phenylenediamine. The process may also be carried out by condensing the said acids and acid derivatives with aromatic primary or secondary amines with no basic side chain'and subsequently introducing a basic side chain into the products thus obtained.
The following examples serve to illustrate my invention, but they are not intended to limit it thereto.
(1) 10.4 g. of para-B-diethylaminoethoxyanilene, dissolved in 40 ccm. of dry acetoneand 15 g. of the chloride of oleic acid dissolved in 20 ccm. of acetone are mixed while cooling. After having allowed themixture acetone, melts at 85 C.87 C. By treating it with-an alkali the free base is obtained as a fat-like mass. The aqueous solutions of'the salts, for instance of the benzoate, the lactate or the' salt of the para-phenolsulfon ic'acid,
yield jellies, even when only slightly. concentrated.
The product has the following formula:
ly added thereto. After'eooling the mass is filtered by suction. The resulting hydrochloride which is obtained in the form of colorless laminae, melts at 108 (l-lll"v C. By treating it with an alkali the base is obtained, which recrystallizes from acetone alcohol in the form of felted needles melting at 82 C.
The product has the following formula:
(3) 11.8 g. of the vdiethylaminoethanol ester of para-aminobenzoic acid are dissolved in 20 ccm. of acetone and there are added 13.7 g. of the chloride of palmitic acid in 20 ccm. of acetone. After cooling, the solution is filtered by suction. The hydrochloride of the new compound, when recrystallized from acetone, is'obtaine'd in the form of white laminae melting at 116 C.
The product has the following formula:
-' v -\C zH6 (4) 22.1 g. of asymmetric methyldiethyl' ammoethyl para phenylenediamine dissolved in ccm. of acetic ester and 30 g. of the chloride of oleic acid in 50 com. of acetic ester are mixed. On cooling, the hydrochloride of the new compound crystallizes in the form of colorless laminae.
The product has the following fomnula:
(5) 64.7 g. of asymmetric ethyldiethylaminoethyl-para-phenlyenediamine in 450 ccm. of dry acetone are gradually mixed with 7 5 g. of the chloride of palmitic acid in 250 ccm..
of acetone. After cooling, the hydrochloride of the new compound crystallizes in the form of white druses melting at 81 C.
The product has the following formula:
I claim 1. The process which consists in causing a derivative of a higher fatty acid of the general formula:
wherein R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms, R stands for a radical of the group consisting of OH, OCH, OC2H OGH2G Hg, C1, NH and R stands for O or NH, to act upon an aromatic polyamino compound of the following general formula:
wherein R stands for an aliphatic residue with a tertiary amino group or for an amino group which has at least one aliphatic residue containing a tertiary nitrogen.
2. The process whlch consists in causing a chloride of a higher fatty acid of the general formula:
wherein R stands for an aliphatic hydrocarbon residue with at least 10 carbon atoms, to act upon an aromatic polyamino compound of the following general formula:
wherein R stands for an aliphatic residue with a tertiary amino group or for an' amino group which has at least one aliphatic residue containing a tertiary nitrogen.
3. The process which consists in causing a chloride of a higher fatty acid of the gen eral formula:
o RO 01 wherein R stands for an aliphatic hydrocarbon resldue containing at least 10 carbon atoms, to act upon a compound of the general formula:
wherein R stands for hydrogen, an alkyl or an aralkyl and R stands for an aliphatic residue containing a tertiary nitrogen atom.
4. The process which consists in causing a chloride of a higher fatty acid of the general formula:
wherein R stands for an aliphatic hydrocar;
bon residue containing at least 10 carbon.
atoms, to act upon a compound of the formula \C2H4N (C2Ht):
wherein R stands for CH 0r C l-I 5. As new products, the compounds of the following formula:
wherein R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms, R stands for O or NH and R stands for an aliphatic residue with a tertiary amino group or for an amino group which contains at least an aliphatic residue with a tertiary nitrogen atom, said products possessing valuable therapeutic and technical properties.
6. As new products, the compounds of the following formula:
wherein R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms, R stands for hydrogen or alkyl and R stands for an aliphatic residue with a tertiary nitrogen, said products possessing valuable therapeutical and technical properties. 7. As new products, the compounds of the following formula:
wherein R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms, said products possessing valuable therapeutical and technical properties.
following formula:
cal and technical properties.
, I Cfls -sa'id products possessing valuable therapeuti- In testimony whereof, I afiix my s' ature.
ROBERT
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1894375A true US1894375A (en) | 1933-01-17 |
Family
ID=3424898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1894375D Expired - Lifetime US1894375A (en) | Basic product and process of making it |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1894375A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3362993A (en) * | 1964-05-07 | 1968-01-09 | Hoffmann La Roche | Substituted benzamides and methods for their preparation |
| EP0282127A2 (en) * | 1987-03-09 | 1988-09-14 | The Procter & Gamble Company | Beta-aminoethyl-substituted phenyl compounds, and anti-inflammatory or analgesic compositions containing them |
-
0
- US US1894375D patent/US1894375A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3362993A (en) * | 1964-05-07 | 1968-01-09 | Hoffmann La Roche | Substituted benzamides and methods for their preparation |
| EP0282127A2 (en) * | 1987-03-09 | 1988-09-14 | The Procter & Gamble Company | Beta-aminoethyl-substituted phenyl compounds, and anti-inflammatory or analgesic compositions containing them |
| EP0282127A3 (en) * | 1987-03-09 | 1990-08-01 | The Procter & Gamble Company | Beta-aminoethyl-substituted phenyl compounds, and anti-inflammatory or analgesic compositions containing them |
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