DE1228613B - Process for the preparation of 2 ', 6'-disubstituted N-alkylpiperidine-2-monocarboxylic acid anilides - Google Patents
Process for the preparation of 2 ', 6'-disubstituted N-alkylpiperidine-2-monocarboxylic acid anilidesInfo
- Publication number
- DE1228613B DE1228613B DEA26583A DEA0026583A DE1228613B DE 1228613 B DE1228613 B DE 1228613B DE A26583 A DEA26583 A DE A26583A DE A0026583 A DEA0026583 A DE A0026583A DE 1228613 B DE1228613 B DE 1228613B
- Authority
- DE
- Germany
- Prior art keywords
- alkylpiperidine
- monocarboxylic acid
- disubstituted
- alkyl
- general formula
- 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.)
- Pending
Links
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 2-chloro-6-aminocaproic acid chloride hydrochloride Chemical compound 0.000 claims description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000003931 anilides Chemical class 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052801 chlorine Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 claims 1
- DDSZWBCJXDRQDU-UHFFFAOYSA-N [N].C1CCNCC1 Chemical group [N].C1CCNCC1 DDSZWBCJXDRQDU-UHFFFAOYSA-N 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 230000037005 anaesthesia Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 230000008595 infiltration Effects 0.000 description 3
- 238000001764 infiltration Methods 0.000 description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229940035674 anesthetics Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- OTHAXHPPJLNGHZ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-6-methylpiperidine-2-carboxamide Chemical compound N1C(C)CCCC1C(=O)NC1=C(C)C=CC=C1C OTHAXHPPJLNGHZ-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 2',6'-disubstituierten N-Alkylpiperidin-2-monocarbonsäureaniliden Gegenstand der Erfindung ist ein Verfahren zur Herstellung von 2',6'-disubstituierten N-Alkylpiperidin-2-monocarbonsäureaniliden, das dadurch gekennzeichnet ist, daß ein an den C-Atomen des Ringes mono- oder dialkylsubstituiertes 2-Chlor-6-aminocapronsäurechloridhydrochlorid in an sich bekannter Weise mit einem Anilin der allgemeinen Formel worin R Methyl oder Chlor, R1 Methyl, X Wasserstoff oder Alkyl bedeutet, umgesetzt wird, das erhaltene Anilid mittels Alkali zu einem Alkylpiperidin-2-monocarbonsäureanilid der allgemeinen Formel worin R, R1 und X die gleiche Bedeutung wie oben haben und R2 und bzw. oder Rs für Alkyl sowie R4 für H oder Alkyl steht, cyclisiert und dieses, wenn R4 gleich H ist, am Piperidin-N-Atom in an sich üblicher Weise zu einer Verbindung der allgemeinen Formel alkyliert wird.Process for the preparation of 2 ', 6'-disubstituted N-alkylpiperidine-2-monocarboxylic acid anilides The invention relates to a process for the preparation of 2', 6'-disubstituted N-alkylpiperidine-2-monocarboxylic acid anilides, which is characterized in that an the carbon atoms of the ring mono- or dialkyl-substituted 2-chloro-6-aminocaproic acid chloride hydrochloride in a manner known per se with an aniline of the general formula where R is methyl or chlorine, R1 is methyl, X is hydrogen or alkyl, the anilide obtained is converted by means of alkali to an alkylpiperidine-2-monocarboxylic acid anilide of the general formula where R, R1 and X have the same meaning as above and R2 and or or Rs is alkyl and R4 is H or alkyl, cyclized and this, when R4 is H, on the piperidine N-atom in a conventional manner to a compound of the general formula is alkylated.
Die auf diese Weise erhaltenen mono- oder disubstituierten N-Alkylpiperidin-2-monocarbonsäureanilide sind erheblich bessere Infiltrationsanästhetika und teilweise sogar bessere Oberfiächenanästhetika als die entsprechenden bekannten, am Piperidinring nicht substituierten Anilide. The mono- or disubstituted N-alkylpiperidine-2-monocarboxylic acid anilides obtained in this way are considerably better infiltration anesthetics and sometimes even better surface anesthetics than the corresponding known anilides which are not substituted on the piperidine ring.
Die Giftigkeit, die Infiltrationsanästhesie und die Oberflächenanästhesie einiger nach dem Verfahren gemäß der Erfindung erhältlicher Verbindungen im Vergleich zu den nicht substituierten Aniliden ergeben die folgende Tabelle. Es werden dabei Verbindungen der allgemeinen Formeln A und B mit verschiedenen Substituenten angeführt.The following table shows the toxicity, the infiltration anesthesia and the surface anesthesia of some compounds obtainable by the process according to the invention in comparison with the unsubstituted anilides. Compounds of the general formulas A and B are used listed with different substituents.
Ferner sind in der Tabelle angegeben die Giftigkeit mit den LD50-Werten
sowie die Wirkungsdauer ED bei der Infiltrationsanästhesie sowie die Wirkungsdauer
EDY bei der Oberflächenanästhesie (Cornealtest). In beiden Fällen wurde der Wert
dadurch erhalten, daß der LD50-Wert der Verbindung nach der Erfindung durch den
LD50-Wert der bekannten nicht substituierten Verbindung dividiert wurde.
Beispiel 1 248,5 Gewichtsteile 2-Chlor-6-amino-5-äthylcapronsäurechloridhydrochlorid läßt man in Aceton mit 141,5 Gewichtsteilen 2-Chlor-6-methylanilin reagieren. Nicht umgesetztes Anilin wird durch Extraktion mit Ather entfernt. Man bringt die wäßrige Lösung mit Lauge auf pH = 12 und läßt sie 24 bis 48 Stunden stehen, wobei der Ringschluß unter Auskristallisierung der Base erfolgt. Die Base wird abgenutscht, gewaschen und getrocknet. Die Alkylierung wird durch Erhitzen der Base auf 100°C mit n-Butylbromid ausgeführt. Es wird Wasser zugesetzt und der Uberschuß an n-Butylbromid mit Ather entfernt. Die Lösung wird mit Kohle behandelt und die alkylierte Base mit Lauge gefällt. Das erhaltene Produkt besteht aus N-n-Butyl-5-äthylpipecolyl-2-chlor-6-methylanilid. Example 1 248.5 parts by weight of 2-chloro-6-amino-5-ethylcaproic acid chloride hydrochloride allowed to react in acetone with 141.5 parts by weight of 2-chloro-6-methylaniline. not converted aniline is removed by extraction with ether. Bring the aqueous Solution with lye to pH = 12 and let it stand for 24 to 48 hours, whereby the ring closure takes place with crystallization of the base. The base is filtered off with suction, washed and dried. The alkylation is carried out by heating the base to 100 ° C with n-butyl bromide executed. Water is added and the excess n-butyl bromide with ether removed. The solution is treated with charcoal and the alkylated base with alkali pleases. The product obtained consists of N-n-butyl-5-ethylpipecolyl-2-chloro-6-methylanilide.
Beispiel 2 234,5 Gewichtsteile 2-Chlor-6-amino-4-methylcapronsäurechloridhydrochlorid werden mit 121 Gewichtsteilen 2,6-Dimethylanilin zur Reaktion gebracht. Nach Aufarbeitung und Alkylierung mit Dimethyl sulfat erhält man N-Methyl-4-methylpipecolyl-2,6-xylidid.Example 2 234.5 parts by weight of 2-chloro-6-amino-4-methylcaproic acid chloride hydrochloride are reacted with 121 parts by weight of 2,6-dimethylaniline. After work-up and alkylation with dimethyl sulfate gives N-methyl-4-methylpipecolyl-2,6-xylidide.
Beispiel 3 Das 2-Chlor-6-amino-4-methylcapronsäurechloridhydrochlorid des Beispiels 1 wird durch dieselbe Menge 2-Chlor-6-amino-5-methylcapronsäurechloridhydrochlorid ersetzt. Als Reaktionsprodukt wird 5 - Methylpipecolyl - 2,6 - dimethylanilin erhalten, das nach Kristallisierung als Hydrochlorid eine Ausbeute von 450/0 und einen Schmelzpunkt von 274 bis 275"C hat. Nach Alkylierung mit Dimethylsulfat wird das N-Methyl- 5 -methylpipecolyl-2,6 -dimethylanilin mit einer Ausbeute von 900/0 in Form eines puls erhalten. Example 3 The 2-chloro-6-amino-4-methylcaproic acid chloride hydrochloride of Example 1 is replaced by the same amount of 2-chloro-6-amino-5-methylcaproic acid chloride hydrochloride replaced. The reaction product obtained is 5-methylpipecolyl-2,6-dimethylaniline, after crystallization as the hydrochloride, a yield of 450/0 and a melting point from 274 to 275 "C. After alkylation with dimethyl sulfate, the N-methyl-5 -methylpipecolyl-2,6-dimethylaniline with a yield of 900/0 in the form of a get pulse.
Beispiel 4 2- Chlor -6- amino -4- methylcapronsäurechloridhydrochlorid wird durch dieselbe Menge 2-Chlor- 6 - amino - 6 - methylcapronsäurechloridhydrochlorid ersetzt. Als Reaktionsprodukt wird 6-Methylpipecolyl-2,6-dimethylanilin erhalten, das nach Kristallisierung als Hydrochlorid eine Ausbeute von 480/0 und einen Schmelzpunkt von 280 bis 282"C hat. Example 4 2-chloro -6-amino -4-methylcaproic acid chloride hydrochloride is replaced by the same amount of 2-chlorine 6 - amino - 6 - methylcaproic acid chloride hydrochloride replaced. The reaction product obtained is 6-methylpipecolyl-2,6-dimethylaniline, after crystallization as the hydrochloride, a yield of 480/0 and a melting point from 280 to 282 "C.
Nach Alkylierung mit Dimethylsulfat wird N-Methyl-6-methylpipecolyl-2,6-dimethylanilin mit einer Ausbeute von 90°/0 in Form eines Ols erhalten.After alkylation with dimethyl sulfate, N-methyl-6-methylpipecolyl-2,6-dimethylaniline is obtained obtained with a yield of 90 ° / 0 in the form of an oil.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE170156 | 1956-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1228613B true DE1228613B (en) | 1966-11-17 |
Family
ID=38526955
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA26584A Pending DE1229091B (en) | 1956-02-22 | 1957-02-14 | Process for the preparation of 2 ', 6'-disubstituted 1-alkylpiperidine-2-monocarboxylic acid anilides |
| DEA26583A Pending DE1228613B (en) | 1956-02-22 | 1957-02-14 | Process for the preparation of 2 ', 6'-disubstituted N-alkylpiperidine-2-monocarboxylic acid anilides |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA26584A Pending DE1229091B (en) | 1956-02-22 | 1957-02-14 | Process for the preparation of 2 ', 6'-disubstituted 1-alkylpiperidine-2-monocarboxylic acid anilides |
Country Status (7)
| Country | Link |
|---|---|
| BE (2) | BE554777A (en) |
| DE (2) | DE1229091B (en) |
| DK (3) | DK87391C (en) |
| ES (1) | ES234060A1 (en) |
| FR (1) | FR1225621A (en) |
| GB (1) | GB799778A (en) |
| NL (1) | NL98233C (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3138614A (en) * | 1961-12-18 | 1964-06-23 | Lilly Co Eli | Salts of 1, 1-dimethyl-3-pyrrolidyl phenyl-2-thienylglycolate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT180259B (en) * | 1952-02-25 | 1954-11-25 | Cilag Ag | Process for the preparation of new basic substituted fatty acid-2-halogen-6-methylanilides and their salts |
-
1957
- 1957-02-06 BE BE554777A patent/BE554777A/en unknown
- 1957-02-08 BE BE554837A patent/BE554837A/en unknown
- 1957-02-11 GB GB4583/57A patent/GB799778A/en not_active Expired
- 1957-02-14 DE DEA26584A patent/DE1229091B/en active Pending
- 1957-02-14 DE DEA26583A patent/DE1228613B/en active Pending
- 1957-02-18 FR FR732024A patent/FR1225621A/en not_active Expired
- 1957-02-21 DK DK65057AA patent/DK87391C/en active
- 1957-02-21 DK DK65157AA patent/DK88970C/en active
- 1957-02-21 NL NL214800A patent/NL98233C/en active
- 1957-02-21 DK DK65257AA patent/DK86988C/en active
- 1957-02-22 ES ES0234060A patent/ES234060A1/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT180259B (en) * | 1952-02-25 | 1954-11-25 | Cilag Ag | Process for the preparation of new basic substituted fatty acid-2-halogen-6-methylanilides and their salts |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1225621A (en) | 1960-07-01 |
| ES234060A1 (en) | 1957-11-01 |
| BE554777A (en) | 1960-01-29 |
| DK88970C (en) | 1960-05-16 |
| NL98233C (en) | 1961-06-15 |
| DE1229091B (en) | 1966-11-24 |
| DK87391C (en) | 1959-06-08 |
| DK86988C (en) | 1959-03-09 |
| BE554837A (en) | 1960-02-12 |
| GB799778A (en) | 1958-08-13 |
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