GB837986A - New piperazine derivatives and process for the preparation thereof - Google Patents
New piperazine derivatives and process for the preparation thereofInfo
- Publication number
- GB837986A GB837986A GB21624/57A GB2162457A GB837986A GB 837986 A GB837986 A GB 837986A GB 21624/57 A GB21624/57 A GB 21624/57A GB 2162457 A GB2162457 A GB 2162457A GB 837986 A GB837986 A GB 837986A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperazine
- chlorobenzhydryloxy
- ethyl
- mono
- alkyl
- 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
- 238000000034 method Methods 0.000 title abstract 3
- 150000004885 piperazines Chemical class 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 9
- -1 hydroxy-ethoxyethyl Chemical group 0.000 abstract 9
- 239000002253 acid Substances 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- LYCMPAUKXOWIMQ-UHFFFAOYSA-N 1-chloro-2-[2-chloroethoxy(phenyl)methyl]benzene Chemical compound ClCCOC(C1=CC=CC=C1)C1=C(Cl)C=CC=C1 LYCMPAUKXOWIMQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- GRVNOUKHAZXMJK-UHFFFAOYSA-N 1-[(2-methylphenyl)methyl]piperazine Chemical class CC1=CC=CC=C1CN1CCNCC1 GRVNOUKHAZXMJK-UHFFFAOYSA-N 0.000 abstract 1
- VTEOTZPEMDQENX-UHFFFAOYSA-N 1-[(3-methylphenyl)methyl]piperazine Chemical compound CC1=CC=CC(CN2CCNCC2)=C1 VTEOTZPEMDQENX-UHFFFAOYSA-N 0.000 abstract 1
- ABYCAKSCMPBUOC-UHFFFAOYSA-N 1-[2-[(2-chlorophenyl)-phenylmethoxy]ethyl]piperazine Chemical compound ClC1=CC=CC=C1C(C=1C=CC=CC=1)OCCN1CCNCC1 ABYCAKSCMPBUOC-UHFFFAOYSA-N 0.000 abstract 1
- URQSCBUMDCEIEJ-UHFFFAOYSA-N 1-[2-chloroethoxy(phenyl)methyl]-2-methylbenzene Chemical compound CC1=CC=CC=C1C(OCCCl)C1=CC=CC=C1 URQSCBUMDCEIEJ-UHFFFAOYSA-N 0.000 abstract 1
- XGAZUUKZVKLBKP-UHFFFAOYSA-N 1-chloro-2-[3-chloropropoxy(phenyl)methyl]benzene Chemical compound ClCCCOC(C1=CC=CC=C1)C1=C(Cl)C=CC=C1 XGAZUUKZVKLBKP-UHFFFAOYSA-N 0.000 abstract 1
- SMAWHVWGCNFFQE-UHFFFAOYSA-N 1-chloro-2-[4-chlorobutoxy(phenyl)methyl]benzene Chemical compound ClCCCCOC(C1=CC=CC=C1)C1=C(Cl)C=CC=C1 SMAWHVWGCNFFQE-UHFFFAOYSA-N 0.000 abstract 1
- SPCJBEYHQMJSEY-UHFFFAOYSA-N 1-chloro-2-[6-chlorohexoxy(phenyl)methyl]benzene Chemical compound ClCCCCCCOC(C1=CC=CC=C1)C1=C(Cl)C=CC=C1 SPCJBEYHQMJSEY-UHFFFAOYSA-N 0.000 abstract 1
- XPDSXKIDJNKIQY-UHFFFAOYSA-N 1-cyclohexylpiperazine Chemical compound C1CCCCC1N1CCNCC1 XPDSXKIDJNKIQY-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- BNCHCCGONFAIQJ-UHFFFAOYSA-N 3-[4-[(2-methylphenyl)methyl]piperazin-1-yl]propan-1-ol Chemical compound OCCCN1CCN(CC1)CC1=C(C=CC=C1)C BNCHCCGONFAIQJ-UHFFFAOYSA-N 0.000 abstract 1
- GJOWSEBTWQNKPC-UHFFFAOYSA-N 3-methyloxiran-2-ol Chemical compound CC1OC1O GJOWSEBTWQNKPC-UHFFFAOYSA-N 0.000 abstract 1
- GAIMKZRGXVVZHT-UHFFFAOYSA-N 3-piperazin-2-ylpropane-1,1-diol Chemical compound OC(CCC1CNCCN1)O GAIMKZRGXVVZHT-UHFFFAOYSA-N 0.000 abstract 1
- GTGCHKRWVHIHLM-UHFFFAOYSA-N 4-[4-[(3-methylphenyl)methyl]piperazin-1-yl]butan-1-ol Chemical compound OCCCCN1CCN(CC1)CC1=CC(=CC=C1)C GTGCHKRWVHIHLM-UHFFFAOYSA-N 0.000 abstract 1
- HXHGULXINZUGJX-UHFFFAOYSA-N 4-chlorobutanol Chemical compound OCCCCCl HXHGULXINZUGJX-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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:0837986/IV (b)/1> (wherein R is a halogen atom or an alkyl radical, R1 is an alkyl, hydroxyalkyl, hydroxyalkoxyalkyl, aralkoxyalkyl or aralkyl radical, any carbocyclic ring of which may be substituted by an alkyl or alkoxy radical or a halogen atom, or R1 is an alkanoyl radical or an aroyl radical which may be halogen substituted, and n is an integer of from 2 to 6), and acid-addition salts thereof; and their preparation by the following methods: (1) reaction of a 1 - mono - [omega - (o - R - benzhydryloxy)-alkyl]-piperazine with an R1-halide, optionally in the presence of a hydrohalic acid acceptor, or with an aldehyde with subsequent reduction of the intermediate product with hydrogen in the presence of Raney nickel, or with an acid chloride to form an N-acyl piperazine which may then be reduced with lithium aluminium hydride to the corresponding N-alkyl- or aralkyl-piperazine; (2) reaction of an omega-(o - R - benzhydryloxy) - alkyl halide with a 1 - mono - R1 - piperazine, optionally in the presence of a hydrohalic acid acceptor; (3) reaction of an o-R-benzhydryl halide with a 1-(omega - hydroxyalkyl) - 4 - R1 - piperazine, optionally in the presence of a hydrohalic acid acceptor; (4) reaction of an o-R-benzhydrol with a 1 - (omega - halogen - alkyl) - 4 - R1-piperazine, optionally in the presence of a hydrohalic acid acceptor; or (5) by building up the R1 chain in several steps, for example by condensing the compound wherein R1 is -(CH2)2OH with ethylene chlorohydrin or ethylene oxide. Examples illustrate the above processes, in which R1 has the values hydroxy-ethoxyethyl, isopropyl, m - methyl - benzyl, acetyl, ethyl, methyl, 2-(p-t-butylbenzyloxy)-ethyl, isopropyl, n- and iso-butyl, 2-hydroxy-ethyl, 2 :3 - dihydroxypropyl, cyclohexyl, 3-methyl - cyclohexyl, benzyl, o - chlorobenzyl, o - methylbenzyl, p - t - butylbenzyl, o - methoxybenzyl, R has the values of chloro and methyl and n the values of 2,3,4- and 6. Hydrochlorides of the products are also described. 2 - (o - Chlorobenzhydryloxy) - ethyl chloride, 2 - (o - methylbenzhydryloxy) - ethyl chloride, 3-(o - chlorobenzhydryloxy) - propyl chloride, 4-(o - chlorobenzhydryloxy) - butyl chloride and 6 - (o - chlorobenzhydryloxy) - hexyl chloride are prepared from the appropriate benzhydrol and chloro-alkanol in presence of concentrated sulphuric acid and benzene. 1 - Mono - [2 - (o - chlorobenzhydryloxy)-ethyl] - piperazine (dihydrochloride also described), is prepared from 2-(o-chlorobenzhydryloxy)-ethyl chloride and piperazine, and 1 - mono - [2 - (o - methylbenzhydryloxy) - ethyl]-1 - [3 - (o - chlorobenzhydryloxy) - propyl] -, 1 - [4 - (o - chlorobenzhydryloxybutyl] - and 1 - [6 - o - chlorobenzhydryloxy) - hexyl] - piperazines are prepared similarly. 1 - Mono - cyclohexyl - piperazine is prepared from cyclohexyl bromide and piperazine, and 1 - (3 - methylcyclohexyl) - and 1 - mono - (o - methylbenzyl) - piperazines are prepared similarly. 1 - Mono - (2 : 3 - dihydroxypropyl - piperazine) is prepared from piperazine and epoxypropanol. 1 - (4 - Hydroxybutyl) - 4 - (m - methylbenzyl)-piperazine is prepared from 1-(m-methylbenzyl)-piperazine and 4-chlorobutanol, and 1-(3-hydroxypropyl) - 4 - (o - methylbenzyl) - piperazine is prepared similarly.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE837986X | 1956-07-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB837986A true GB837986A (en) | 1960-06-22 |
Family
ID=3881891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21624/57A Expired GB837986A (en) | 1956-07-10 | 1957-07-08 | New piperazine derivatives and process for the preparation thereof |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB837986A (en) |
| MY (1) | MY6100003A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2374318A1 (en) * | 1976-12-14 | 1978-07-13 | Gist Brocades Nv | 1-Benzhydryl:oxy-alkyl-4-phenylalkyl- or cinnamyl-piperazine derivs. - with dopaminergic, anticholinergic and antiparkinson activity (BE 14.6.78) |
| US4202896A (en) | 1976-12-14 | 1980-05-13 | Gist-Brocades N.V. | N-Benzhydryloxyethyl-N-phenylpropyl-piperazines |
| EP0243903A1 (en) * | 1986-04-28 | 1987-11-04 | Richter Gedeon Vegyészeti Gyár R.T. | Optionally substituted 1-(omega[bis(phenyl)-alcoxy]-alkyl)-4-(alkenyl)piperazines and -4-(alkynyl)piperazines, process for their preparation and medicines containing them |
| US4868184A (en) * | 1986-04-28 | 1989-09-19 | Richter Gedeon Vegyeszeti Gyar | Benzhydrylpiperazines pharmaceutical compositions thereof and method of use |
| EP0566189A1 (en) * | 1992-04-13 | 1993-10-20 | Akzo N.V. | Psychotropic piperazine derivative |
-
1957
- 1957-07-08 GB GB21624/57A patent/GB837986A/en not_active Expired
-
1961
- 1961-12-30 MY MY3/61A patent/MY6100003A/en unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2374318A1 (en) * | 1976-12-14 | 1978-07-13 | Gist Brocades Nv | 1-Benzhydryl:oxy-alkyl-4-phenylalkyl- or cinnamyl-piperazine derivs. - with dopaminergic, anticholinergic and antiparkinson activity (BE 14.6.78) |
| US4202896A (en) | 1976-12-14 | 1980-05-13 | Gist-Brocades N.V. | N-Benzhydryloxyethyl-N-phenylpropyl-piperazines |
| US4874765A (en) * | 1986-04-22 | 1989-10-17 | Richter Gedeon Vegyeszeti Gyar | 1,4-Disubstituted piperazines having dopaminergic activity |
| EP0243903A1 (en) * | 1986-04-28 | 1987-11-04 | Richter Gedeon Vegyészeti Gyár R.T. | Optionally substituted 1-(omega[bis(phenyl)-alcoxy]-alkyl)-4-(alkenyl)piperazines and -4-(alkynyl)piperazines, process for their preparation and medicines containing them |
| US4868184A (en) * | 1986-04-28 | 1989-09-19 | Richter Gedeon Vegyeszeti Gyar | Benzhydrylpiperazines pharmaceutical compositions thereof and method of use |
| EP0566189A1 (en) * | 1992-04-13 | 1993-10-20 | Akzo N.V. | Psychotropic piperazine derivative |
| US5281598A (en) * | 1992-04-13 | 1994-01-25 | Akzo N.V. | Piperazine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| MY6100003A (en) | 1961-12-31 |
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