GB753166A - Improvements in or relating to substituted piperazines - Google Patents
Improvements in or relating to substituted piperazinesInfo
- Publication number
- GB753166A GB753166A GB11399/54A GB1139954A GB753166A GB 753166 A GB753166 A GB 753166A GB 11399/54 A GB11399/54 A GB 11399/54A GB 1139954 A GB1139954 A GB 1139954A GB 753166 A GB753166 A GB 753166A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenylpiperazine
- phenyl
- piperazine
- alkyl
- trimethyl
- 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
- C07D295/027—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 containing only one hetero ring
- C07D295/033—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 containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
Abstract
The invention comprises 1-alkyl-4-phenyl-piperazines where the alkyl group has 5-9 carbon atoms, and acid addition salts thereof. These may be prepared by (1) alkylating N-phenyl-piperazine; (2) reacting N-alkyl-di-ethanolamines with aniline; or (3) reacting N-phenyl-diethanolamine with primary alkyl-amines of 5-9 carbon atoms. The products are isolated as hydrochloride or sulphate salts. N-Phenyl-piperazine can be obtained from aniline and diethanolamine or by other methods described in the literature. In the examples: (1) 1 - (3:3 - dimethylpentyl) - 4 - phenylpiperazine is made from N-phenyl-piperazine and 1-chloro - 3:3 - dimethylpentane; (2) 1 - (3:3 - dimethylbutyl) - 4 - phenylpiperazine is prepared from N-phenyl-piperazine and 1-chloro-3:3-dimethylbutane; (3) 1-(3:5:5-trimethyl-hexyl) - 4 - phenylpiperazine is obtained from N-phenylpiperazine and 3:5:5-trimethylhexyl toluene - p - sulphonate; (4) 1-(2-ethylbutyl)-4-phenylpiperazine is made by catalytic hydrogenation of a mixture of N-phenylpiperazine and 2 - ethyl - butyraldehyde; (5) 1 - (3:4:4 - trimethylpentyl) - 4 - phenylpiperazine is obtained similarly from b :g :g -trimethyl-valeraldehyde. The toluene-p-sulphonic ester of 3:5:5-trimethyl-hexanol is prepared from the alcohol and toluene-p-sulphonyl chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US753166XA | 1953-05-22 | 1953-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB753166A true GB753166A (en) | 1956-07-18 |
Family
ID=22124919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11399/54A Expired GB753166A (en) | 1953-05-22 | 1954-04-20 | Improvements in or relating to substituted piperazines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB753166A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1078130B (en) * | 1956-10-22 | 1960-03-24 | Parke Davis & Co | Process for the preparation of phenylpiperazines with a dampening effect on the central nervous system |
| DE1088058B (en) * | 1956-08-21 | 1960-09-01 | Davis & Company | Process for the preparation of sympatholytically acting N-o-halophenyl-N'-acylamino-alkylpiperazines and their acid salts |
| US3106557A (en) * | 1960-07-20 | 1963-10-08 | Union Carbide Corp | Process for the preparation of nu-phenylpiperazines |
| WO2003066604A3 (en) * | 2002-02-05 | 2003-12-04 | Novo Nordisk As | Novel aryl- and heteroarylpiperazines |
| US8318927B2 (en) | 2006-05-23 | 2012-11-27 | High Point Pharmaceuticals, Llc | 6-(4-cyclopropylpiperazin-1-yl)-2′-methyl-[3, 4′]-bipyridine and its uses as a medicament |
| US8344001B2 (en) | 2007-06-11 | 2013-01-01 | High Point Pharmaceuticals, Llc | Heterocyclic H3 antagonists |
| US8378097B2 (en) | 2006-05-29 | 2013-02-19 | High Point Pharmaceuticals, Llc | 3-(1,3-benzodioxol-5-yl)-6-(4-cyclopropylpiperazin-1-yl)-pyridazine, its salts and solvates and its use as histamine H3 receptor antagonist |
| US8501739B2 (en) | 2005-07-04 | 2013-08-06 | High Point Pharmaceuticals, Llc | Medicaments |
-
1954
- 1954-04-20 GB GB11399/54A patent/GB753166A/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1088058B (en) * | 1956-08-21 | 1960-09-01 | Davis & Company | Process for the preparation of sympatholytically acting N-o-halophenyl-N'-acylamino-alkylpiperazines and their acid salts |
| DE1078130B (en) * | 1956-10-22 | 1960-03-24 | Parke Davis & Co | Process for the preparation of phenylpiperazines with a dampening effect on the central nervous system |
| US3106557A (en) * | 1960-07-20 | 1963-10-08 | Union Carbide Corp | Process for the preparation of nu-phenylpiperazines |
| WO2003066604A3 (en) * | 2002-02-05 | 2003-12-04 | Novo Nordisk As | Novel aryl- and heteroarylpiperazines |
| JP2005533747A (en) * | 2002-02-05 | 2005-11-10 | ノボ ノルディスク アクティーゼルスカブ | Novel aryl and heteroaryl piperazines |
| US8501739B2 (en) | 2005-07-04 | 2013-08-06 | High Point Pharmaceuticals, Llc | Medicaments |
| US8846677B2 (en) | 2005-07-04 | 2014-09-30 | High Point Pharmaceuticals, Llc | Medicaments |
| US8318927B2 (en) | 2006-05-23 | 2012-11-27 | High Point Pharmaceuticals, Llc | 6-(4-cyclopropylpiperazin-1-yl)-2′-methyl-[3, 4′]-bipyridine and its uses as a medicament |
| US8378097B2 (en) | 2006-05-29 | 2013-02-19 | High Point Pharmaceuticals, Llc | 3-(1,3-benzodioxol-5-yl)-6-(4-cyclopropylpiperazin-1-yl)-pyridazine, its salts and solvates and its use as histamine H3 receptor antagonist |
| US8344001B2 (en) | 2007-06-11 | 2013-01-01 | High Point Pharmaceuticals, Llc | Heterocyclic H3 antagonists |
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