GB738690A - Improvements in or relating to derivatives of piperazine and the manufacture thereof - Google Patents
Improvements in or relating to derivatives of piperazine and the manufacture thereofInfo
- Publication number
- GB738690A GB738690A GB13210/53A GB1321053A GB738690A GB 738690 A GB738690 A GB 738690A GB 13210/53 A GB13210/53 A GB 13210/53A GB 1321053 A GB1321053 A GB 1321053A GB 738690 A GB738690 A GB 738690A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iodide
- benzhydryl
- methyl
- piperazine
- ethyl
- 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
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
- C07D295/037—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 with quaternary ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0738690/IV (b)/1> wherein Y is a phenyl or cyclohexyl radical, R is a methyl group or hydrogen and R1 and R11 are alkyl groups having from 1 to 3 carbon atoms and wherein the sum of the carbon atoms in the cation is at least 20 and not more than 23 and X is the anion of an acid that is not itself toxic or addition salts thereof. Such compounds are obtained by reacting the corresponding tertiary bases of the formula <FORM:0738690/IV (b)/2> or in the case where R1 and R11 are alike piperazine compounds of the general formula <FORM:0738690/IV (b)/3> with a compound of the formula R11X. The anion X can be for example an iodide, bromide, chloride, sulphate, ethyl sulphonate or malate radical. In examples (1a) benzhydryl chloride and 2,5-dimethyl piperazine are reacted to give 2,5-dimethyl-4-benzhydryl-piperazine which (1b) is reacted with formaldehyde and formic acid to give 1,2,5-trimethyl-4-benzhydryl piperazine and the latter compound is quaternated (1c) with methyl iodide to give 1,1,2,5-tetramethyl-4-benzhydryl piperazinium iodide. The methiodide can be converted to the methochloride by the action of silver chloride. In (1c) the quaternation may also be effected with methyl bromide or dimethyl sulphate; (2) the tertiary base from (1b) is quaternated with ethyl iodide yielding 1,2,5 - trimethyl - 1 - ethyl - 4 - benzhydryl piperazinium iodide; (3) 1,1-diethyl-2,5-dimethyl-4-benzhydryl piperazinium iodide is obtained by reacting 2,5-dimethyl-4-benzhydryl piperazine with ethyl iodide; (4) 1-ethyl-1-methyl - 4 - benzhydryl piperazinium iodide is prepared by reacting benzhydryl methyl piperazine with ethyl iodide; (5) 1-ethyl-1-methyl-4-(a - cyclohexylbenzyl)piperazinium iodide is prepared by reacting 1 - methyl - 4(a - cyclohexylbenzyl)piperazine with ethyl iodide; (6) 1,1 - diethyl - 4 - benzhydryl piperazinium iodide is prepared by reacting benzhydryl piperazine with ethyl iodide. Also prepared by similar methods are 1,1-diethyl-4-(a -cyclohexylbenzyl)piperazinium iodide, 1-isopropyl-1-methyl - 4 - (a - cyclohexylbenzyl)piperazinium iodide, 1 - isopropyl - 1 - methyl - 4 - benzhydryl piperazinium iodide and 1-methyl-1-propyl-4-(a -cyclohexylbenzyl)piperazinium iodide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US738690XA | 1952-05-13 | 1952-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB738690A true GB738690A (en) | 1955-10-19 |
Family
ID=22116290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13210/53A Expired GB738690A (en) | 1952-05-13 | 1953-05-12 | Improvements in or relating to derivatives of piperazine and the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB738690A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2961442A (en) * | 1957-05-28 | 1960-11-22 | Abbott Lab | Beta-substituted-ethyl piperazines |
-
1953
- 1953-05-12 GB GB13210/53A patent/GB738690A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2961442A (en) * | 1957-05-28 | 1960-11-22 | Abbott Lab | Beta-substituted-ethyl piperazines |
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