CA1050541A - Process for the preparation of benzylamines - Google Patents
Process for the preparation of benzylaminesInfo
- Publication number
- CA1050541A CA1050541A CA208,639A CA208639A CA1050541A CA 1050541 A CA1050541 A CA 1050541A CA 208639 A CA208639 A CA 208639A CA 1050541 A CA1050541 A CA 1050541A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- group
- compound
- benzyl
- 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.)
- Expired
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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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
This invention relates to a new process for the preparation of certain 2-amino- and 2-benzoylamino-benzylamine derivatives possessing valuable physiological properties in particular an antiussive, secretolytic an/or respiration stimulating effect. The new process comprises the reaction of the corresponding 2-amino-or 2-benzoylamino-benzylammonium or benzylpyridinium compound with an appropriate amine and the optional subsequent conversion of the compound thus prepared into an acid addition salt thereof. The new process is exemplified.
This invention relates to a new process for the preparation of certain 2-amino- and 2-benzoylamino-benzylamine derivatives possessing valuable physiological properties in particular an antiussive, secretolytic an/or respiration stimulating effect. The new process comprises the reaction of the corresponding 2-amino-or 2-benzoylamino-benzylammonium or benzylpyridinium compound with an appropriate amine and the optional subsequent conversion of the compound thus prepared into an acid addition salt thereof. The new process is exemplified.
Description
This invention relates to a new process for the preparation of certain 2-amino- and 2-benzoylaminobenzylamine derivatives having valuable physiological properties, in particular an antitussive, secretolytic and/or respiration stimulating activity British Patent Specifications 968,254, 1,098,140 and 1,178,034 describe inter alia benzylamines of general formula R2 (I) CH2 - N \ R
Ha 4 wherein Hal represents a chlorine or bromine atom, Rl represents a hydrogen, chlorine or bromine atom, R2 represents a hydrogen atom or an alkyl group with 1 to 3 carbon atoms, and either R3 represents a cyclohexyl or hydroxy-cyclohexyl group and R4 represents a hydrogen atom, or R3 represents an isopropylaminocarbonylmethyl or morpholinocarbonylmethyl group and R4 representsa hydrogen atom or a benzoyl group) and pharmaceutically acceptable acid addition salts thereof, and also processes for their preparation.
It is known from the literature that quaternary ammonium compounds are moderately strong alkylating agents (see for exan~ple Houben-Weyl XI, part ~ :
Ha 4 wherein Hal represents a chlorine or bromine atom, Rl represents a hydrogen, chlorine or bromine atom, R2 represents a hydrogen atom or an alkyl group with 1 to 3 carbon atoms, and either R3 represents a cyclohexyl or hydroxy-cyclohexyl group and R4 represents a hydrogen atom, or R3 represents an isopropylaminocarbonylmethyl or morpholinocarbonylmethyl group and R4 representsa hydrogen atom or a benzoyl group) and pharmaceutically acceptable acid addition salts thereof, and also processes for their preparation.
It is known from the literature that quaternary ammonium compounds are moderately strong alkylating agents (see for exan~ple Houben-Weyl XI, part ~ :
2, page 633). However according to the present invention we have found that compounds o general formula I as hereinbefore defined and acid addition salts thereo may be prepared according to a process which comprises reacting 20. a compound o formula , ~ . .
, .il .
_ _ YC ~n ,~ "~
_ n (wherein Hal, Rl and R4 are as hereinbefore defined, X represents a tri~low- ;
eralkyl) ammonium or pyridinium group, Y represents an inorganic anion and n represents the valency of the said anion with a compound of formula H - N
~w~erein R2 and R3 are as hereinbefore defined~, and, if desired, subsequently converting a compound of formula I thereby obtained into an acid addition ; salt t~ereof.
~, Using the process according to the invention we have prepared com-pounds of general formula I as hereinbefore defm ed and acid addition salts ;
thereof in almost quantitative yield.
The reaction is preferably effected in the presence of an excess of the amine of formula III used, which excess acts as solvent. The reaction may also be effected in the absence of a solvent. The reaction is conveni-ently effec~ed at elevated temperatures, for example at temperatur0s from 100 to 200C, preferably at temperatures from 140 to 160C. ~ ;
.; , T'ne compounds of general formula I obtained may, if desired, be subsequently converted into their acid addition salts, preferahly t~eir 'r physiologically compatible acid addition salts with inorganic or organic acids.
Suitable acids include for example hydrochloric acid, hydrobromic acid, sul-furic acid, phosphoric acid, lactic acid, citric acid and maleic acid.
The compound of general formula II used as starting material ~s Fonveniently in the form of a~h~lid~;and.~ for example be obtained ~y , . .
~L~5~54~
reaction of the corresponding benzylamine with an appropriate alkylating agent, for example methyl iodide, or by reaction of the corresponding benzyl halide with pyridine.
The following Examples serve to illustrate the new process accord-ing to the invention:
Example 1 2-Amino-3,5-dibromo-N-~trans-4-hvdroxY-cYclohexYl)-benzylamine _ 4.5 g ~0.01 mol) of N-(2-amino-3,5-dibromo-benzyl)-trimethylammon-ium iodide and 10 g of trans-4-amino-cyclohexanol were heated for 1 hour at 150C. After cooling, chloroform and 2N sodium hydroxide solution were added and the reac~ion mixture was shaken vigorously. The organic layer was separated and the alkaline layer was again extracted with chloroform. The chloroform extracts were dried with sodium sulfate and evaporated in vacuo.
The residue was dissolved in absolute ethanol and a small quantity of ether and was then acidified with ethanolic hydrochlorir acid, whereupon 2-amino-, 3,5-dibromo-N-(trans-4-hydroxy-cyclohexyl)-benzylamine hydrochloride crystal-lized out.
Yield: 3.9 g (94.0% of theory), m.p.: 233 - 234.5C ~decomp.).
Example 2 i 2-Amino N~yclohexyl-3,5-dibromo-N-methyl-benzylamine .
M.p. of the hydrochloride: 232 - 235C (decomp.). Prepared from N~(2-amino-3,5-dibromo-benzyl)-trimethyl-ammonium iodide and N-methyl-cyclohexylamine analogously to Example 1.
~ield: 92.7% of theory.
Example 3 i 2-Benzoylamino-6-chloro-N-methyl-N-morpholinocarbonylmethyl-benzylamine M.p. of the hydrochloride: 206-208C (decomp.). Prepared from N-(2-benzoylamino-6-chloro-benzyl)-trimethyl-ammonium bromide and sarcosine-morpholide analogously to Example 1.
Yield: 81.0% of theory.
, .il .
_ _ YC ~n ,~ "~
_ n (wherein Hal, Rl and R4 are as hereinbefore defined, X represents a tri~low- ;
eralkyl) ammonium or pyridinium group, Y represents an inorganic anion and n represents the valency of the said anion with a compound of formula H - N
~w~erein R2 and R3 are as hereinbefore defined~, and, if desired, subsequently converting a compound of formula I thereby obtained into an acid addition ; salt t~ereof.
~, Using the process according to the invention we have prepared com-pounds of general formula I as hereinbefore defm ed and acid addition salts ;
thereof in almost quantitative yield.
The reaction is preferably effected in the presence of an excess of the amine of formula III used, which excess acts as solvent. The reaction may also be effected in the absence of a solvent. The reaction is conveni-ently effec~ed at elevated temperatures, for example at temperatur0s from 100 to 200C, preferably at temperatures from 140 to 160C. ~ ;
.; , T'ne compounds of general formula I obtained may, if desired, be subsequently converted into their acid addition salts, preferahly t~eir 'r physiologically compatible acid addition salts with inorganic or organic acids.
Suitable acids include for example hydrochloric acid, hydrobromic acid, sul-furic acid, phosphoric acid, lactic acid, citric acid and maleic acid.
The compound of general formula II used as starting material ~s Fonveniently in the form of a~h~lid~;and.~ for example be obtained ~y , . .
~L~5~54~
reaction of the corresponding benzylamine with an appropriate alkylating agent, for example methyl iodide, or by reaction of the corresponding benzyl halide with pyridine.
The following Examples serve to illustrate the new process accord-ing to the invention:
Example 1 2-Amino-3,5-dibromo-N-~trans-4-hvdroxY-cYclohexYl)-benzylamine _ 4.5 g ~0.01 mol) of N-(2-amino-3,5-dibromo-benzyl)-trimethylammon-ium iodide and 10 g of trans-4-amino-cyclohexanol were heated for 1 hour at 150C. After cooling, chloroform and 2N sodium hydroxide solution were added and the reac~ion mixture was shaken vigorously. The organic layer was separated and the alkaline layer was again extracted with chloroform. The chloroform extracts were dried with sodium sulfate and evaporated in vacuo.
The residue was dissolved in absolute ethanol and a small quantity of ether and was then acidified with ethanolic hydrochlorir acid, whereupon 2-amino-, 3,5-dibromo-N-(trans-4-hydroxy-cyclohexyl)-benzylamine hydrochloride crystal-lized out.
Yield: 3.9 g (94.0% of theory), m.p.: 233 - 234.5C ~decomp.).
Example 2 i 2-Amino N~yclohexyl-3,5-dibromo-N-methyl-benzylamine .
M.p. of the hydrochloride: 232 - 235C (decomp.). Prepared from N~(2-amino-3,5-dibromo-benzyl)-trimethyl-ammonium iodide and N-methyl-cyclohexylamine analogously to Example 1.
~ield: 92.7% of theory.
Example 3 i 2-Benzoylamino-6-chloro-N-methyl-N-morpholinocarbonylmethyl-benzylamine M.p. of the hydrochloride: 206-208C (decomp.). Prepared from N-(2-benzoylamino-6-chloro-benzyl)-trimethyl-ammonium bromide and sarcosine-morpholide analogously to Example 1.
Yield: 81.0% of theory.
- 3 -.
, ,. , : . .
2-Benzoylamino-6-chloro-N-methyl-N-morpholinocarbonylmethyl-benzylamine ; 10 g of N-~2-benzoylamino-6-chloro-benzyl)-pyridinium bromide and 25 ml of sarcosine-morpholide were hea~ed for 2~ hours at 140C. After cooling, the reaction mixture was diluted with water and extrac~ed with ethyl acetate. The ethyl acetate extract was washed with water, dried over magnesium sulfate and evaporated to dryness in vacuo. The oily evaporation residue was crystallized with ether. 8.0 g (74.0% of theory) of 2 benzoy-lamino-6-chloro-N-methyl-N-morpholinocarbonylmethyl-benzylamine of m.p.
122.5 - 123C were thùs obtained.
Example 5 2-Amino-N-cyclohexyl-3,5-dibromo-N-meth~l-benzylamine , - M.p. of the hydrochloride: 232 -235 C ~decomp.).
Prepared from N-~2-amino-3,5-dibromo-benzyl)-pyridinium bromide and N-methyl-cyclohexylamine analogously to Example 4.
Yield: 81.3% of theory.
., :
Example 6 2-Amino-3,5-dibromo-N-~trans-4-hydroxy-cyclohexyl~-benzylamine ., . . . , ~ .
M.p. of the hydrochloride: 233-234.5C ~decomp.).
Prepared from N-~2-amino-3,5-dibromo-benzyl)-pyridinium bromide and trans-4-amino-cyclohexanol analogously to Example 4.
Yield: 87.5% of theory.
Example 7 2-Benzoylamino-6-chloro-N-isopropy~l-N-morp~iolinoca-r-bonyl-_ethyllienzylamIne ~' M.p.: 125 - 127C.
I Prepared from N-~2-benzoylamino-6-chloro-benz~l)-pyridinium bromide and N-isopropyl-glycine-morpholide analogously to Example 4.
Yeild: 76.2% of theory.
! Example 8 - ... .
2-Benzoylamino-4-chloro-N-methyl-N-iso~ropylaminocarbonyl-methylbenzylamine M.p.: 140 - 142C.
Prepared from N-~2-benzoylamino-4-chloro-benzyl~-pyridinium bromide and .
~5~54~
sarcosine-isoproylamide analogously to Example 4.
Example 9 2-Benzoylamino-6-bromo-N-methyl-N-morpholinocarbonylmethyl-benzylamine M.p.: 159 - 161C.
Prepared from N-(2-Benzoylamino-6-bromo-benzyl)-pyridinium bromide and sarcosine-morpholide analogously to Example 4.
Yield: 70.3% of theory.
' .
.' ' .~ :
. ' .
: , , ' . , ,, ,: .
,~. . , . . . ,. , ~
, ,. , : . .
2-Benzoylamino-6-chloro-N-methyl-N-morpholinocarbonylmethyl-benzylamine ; 10 g of N-~2-benzoylamino-6-chloro-benzyl)-pyridinium bromide and 25 ml of sarcosine-morpholide were hea~ed for 2~ hours at 140C. After cooling, the reaction mixture was diluted with water and extrac~ed with ethyl acetate. The ethyl acetate extract was washed with water, dried over magnesium sulfate and evaporated to dryness in vacuo. The oily evaporation residue was crystallized with ether. 8.0 g (74.0% of theory) of 2 benzoy-lamino-6-chloro-N-methyl-N-morpholinocarbonylmethyl-benzylamine of m.p.
122.5 - 123C were thùs obtained.
Example 5 2-Amino-N-cyclohexyl-3,5-dibromo-N-meth~l-benzylamine , - M.p. of the hydrochloride: 232 -235 C ~decomp.).
Prepared from N-~2-amino-3,5-dibromo-benzyl)-pyridinium bromide and N-methyl-cyclohexylamine analogously to Example 4.
Yield: 81.3% of theory.
., :
Example 6 2-Amino-3,5-dibromo-N-~trans-4-hydroxy-cyclohexyl~-benzylamine ., . . . , ~ .
M.p. of the hydrochloride: 233-234.5C ~decomp.).
Prepared from N-~2-amino-3,5-dibromo-benzyl)-pyridinium bromide and trans-4-amino-cyclohexanol analogously to Example 4.
Yield: 87.5% of theory.
Example 7 2-Benzoylamino-6-chloro-N-isopropy~l-N-morp~iolinoca-r-bonyl-_ethyllienzylamIne ~' M.p.: 125 - 127C.
I Prepared from N-~2-benzoylamino-6-chloro-benz~l)-pyridinium bromide and N-isopropyl-glycine-morpholide analogously to Example 4.
Yeild: 76.2% of theory.
! Example 8 - ... .
2-Benzoylamino-4-chloro-N-methyl-N-iso~ropylaminocarbonyl-methylbenzylamine M.p.: 140 - 142C.
Prepared from N-~2-benzoylamino-4-chloro-benzyl~-pyridinium bromide and .
~5~54~
sarcosine-isoproylamide analogously to Example 4.
Example 9 2-Benzoylamino-6-bromo-N-methyl-N-morpholinocarbonylmethyl-benzylamine M.p.: 159 - 161C.
Prepared from N-(2-Benzoylamino-6-bromo-benzyl)-pyridinium bromide and sarcosine-morpholide analogously to Example 4.
Yield: 70.3% of theory.
' .
.' ' .~ :
. ' .
: , , ' . , ,, ,: .
,~. . , . . . ,. , ~
Claims (11)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1, A process for the preparation of compounds of general formula (I) (wherein Hal represents a chlorine or bromine atom, R1 represents a hydrogen, chlorine or bromine atom, R2 represents a hydrogen atom or an alkyl group with 1 to 3 carbon atoms and either R3 represents a cyclohexyl or hydroxycyclo-hexyl group and R4 represents a hydrogen atom, or R3 represents an isopropyl-aminocarbonylmethyl or morpholinocarbonylmethyl group and R4 represents a hydrogen atom or benzoyl group) and pharmaceutically acceptable acid addition salts thereof which comprises reacting a compound of formula (II) (wherein Hal, R1 and R4 are as hereinbefore defined, X+ represents a tri(loweralkyl) ammonium or pyridinium group, Y represents an inorganic anion and n represents the valency of the said anion, with a compound of formula (III) (wherein R2 and R3 are as hereinbefore defined) and, if desired, subsequently converting a compound of formula I thereby obtained into a pharmaceutically acid addition salt thereof.
2. A process as claimed in claim 1 wherein the reaction is effected in the presence of an excess of the compound of formula III used.
3. A process as claimed in claim 1 or claim 2 wherein the reaction is effected at temperatures from 100 to 200°C.
4. A process as claimed in claim 1 or claim 2 wherein the reaction is effected at temperatures from 140 to 160°C.
5. A process as claimed in claim 1 wherein the compound of formula II used is in the form of a halide.
6. A process according to claim 1 in which Hal represents a bromine atom attached in the 3-position, R1 is a bromine atom attached in the 5-position, R2 and R4 are hydrogen atoms, and R3 represents a trans-4-hydroxy-cyclohexyl group.
7. A process for the preparation of 2-amino-3,5-dibromo-N-(trans-4-hydroxy-cyclohexyl)-benzylamine and its hydrochloride which comprises reacting N-(2-amino-3,5-dibromo-benzyl)-trimethylammonium iodide or N-(2-amino-3,5-dibromobenzyl)pyridinium bromide with trans-4-aminocyclohexanol and when the hydrochloride is required reacting the base so obtained with hydrogen chloride.
8. A process according to claim 1 in which Hal represents a bramine atom attached in the 3-position, R1 is a bromine atom attached in the 5-position, R2 represents a methyl group, R3 represents a cyclohexyl group and R4 represents a hydrogen atom.
9. A process for the preparation of 2-amino-N-cyclohexyl-3,5-dibramo-N-methyl-benzylamine and its hydrochlaride which comprises reacting N-(2-amino-3,5-dibromo-benzyl)-trimethyl-ammonium iodide or N-(2-amino-3,5-dibromo-benzyl)-pyridinium bromide with N-methylcyclohexylamine and when the hydrochloride is required reacting the base so obtained with hydrogen chloride.
10. A process according to claim 1 in which Hal is a chlorine atom in the 6-position, R1 represents a hydrogen atom, R2 represents a methyl group, R3 represents a morpholinocarbonylmethyl group and R4 represents a benzoyl group.
11. A process for the preparation of 2-benzoylamino-6-chloro-N-methyl-N-morpholinocarbonylmethyl-benzylamine which comprises reacting N-(2-benzoyl-amino-6-chloro-benzyl)-trimethyl-ammonium bromide or N-(2-benzoylamino-6-chloro-benzyl)-pyridinium bromide with sarcosine-morpholide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742402577 DE2402577C3 (en) | 1974-01-19 | Process for the preparation of benzylamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050541A true CA1050541A (en) | 1979-03-13 |
Family
ID=5905201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA208,639A Expired CA1050541A (en) | 1974-01-19 | 1974-09-06 | Process for the preparation of benzylamines |
Country Status (14)
| Country | Link |
|---|---|
| JP (2) | JPS50101329A (en) |
| AT (1) | AT327876B (en) |
| BG (1) | BG22385A4 (en) |
| CA (1) | CA1050541A (en) |
| CH (1) | CH612663A5 (en) |
| CS (1) | CS167213B2 (en) |
| DK (1) | DK473174A (en) |
| ES (1) | ES429772A2 (en) |
| FI (1) | FI60552C (en) |
| HU (1) | HU167562B (en) |
| NL (1) | NL7410822A (en) |
| PL (1) | PL91730B1 (en) |
| SE (1) | SE439157B (en) |
| YU (1) | YU37110B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT332375B (en) * | 1973-04-13 | 1976-09-27 | Thomae Gmbh Dr K | PROCESS FOR THE PRODUCTION OF NEW AMINOBENZYLAMINES AND THEIR ACID ADDITION SALTS |
-
1974
- 1974-08-08 HU HUBO001513 patent/HU167562B/hu unknown
- 1974-08-08 AT AT651074A patent/AT327876B/en active
- 1974-08-13 NL NL7410822A patent/NL7410822A/en not_active Application Discontinuation
- 1974-08-22 FI FI247174A patent/FI60552C/en active
- 1974-09-05 ES ES429772A patent/ES429772A2/en not_active Expired
- 1974-09-05 YU YU239374A patent/YU37110B/en unknown
- 1974-09-06 DK DK473174A patent/DK473174A/da not_active Application Discontinuation
- 1974-09-06 SE SE7411314A patent/SE439157B/en not_active IP Right Cessation
- 1974-09-06 CA CA208,639A patent/CA1050541A/en not_active Expired
- 1974-09-06 JP JP10286174A patent/JPS50101329A/ja active Pending
- 1974-09-06 CH CH1218874A patent/CH612663A5/en not_active IP Right Cessation
- 1974-09-07 PL PL17395974A patent/PL91730B1/pl unknown
- 1974-09-07 BG BG027656A patent/BG22385A4/en not_active Expired
- 1974-09-13 CS CS631374A patent/CS167213B2/cs unknown
-
1977
- 1977-06-29 JP JP7769277A patent/JPS5353624A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL7410822A (en) | 1975-07-22 |
| FI60552C (en) | 1982-02-10 |
| ATA651074A (en) | 1975-05-15 |
| SE439157B (en) | 1985-06-03 |
| FI60552B (en) | 1981-10-30 |
| YU239374A (en) | 1983-04-27 |
| ES429772A2 (en) | 1977-03-16 |
| YU37110B (en) | 1984-08-31 |
| SE7411314L (en) | 1975-07-21 |
| JPS50101329A (en) | 1975-08-11 |
| FI247174A (en) | 1975-07-20 |
| BG22385A4 (en) | 1977-02-20 |
| DE2402577A1 (en) | 1975-12-18 |
| JPS5353624A (en) | 1978-05-16 |
| PL91730B1 (en) | 1977-03-31 |
| DE2402577B2 (en) | 1976-09-02 |
| CH612663A5 (en) | 1979-08-15 |
| DK473174A (en) | 1975-09-08 |
| JPS568022B2 (en) | 1981-02-20 |
| HU167562B (en) | 1975-11-28 |
| AT327876B (en) | 1976-02-25 |
| CS167213B2 (en) | 1976-04-29 |
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