BE549420A - - Google Patents
Info
- Publication number
- BE549420A BE549420A BE549420DA BE549420A BE 549420 A BE549420 A BE 549420A BE 549420D A BE549420D A BE 549420DA BE 549420 A BE549420 A BE 549420A
- Authority
- BE
- Belgium
- Prior art keywords
- piperazine
- chlorobenzhydryloxy
- ethyl7
- mono
- ethyl
- Prior art date
Links
- -1 carboxylic acid chloride Chemical class 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 16
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-Chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 claims description 3
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 claims description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 150000004885 piperazines Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 229940066771 systemic antihistamines Piperazine derivatives Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 7
- GMRODCVDNXSFAA-UHFFFAOYSA-N 1,3-dimethylbenzene Chemical group [CH2]C1=CC=CC(C)=C1 GMRODCVDNXSFAA-UHFFFAOYSA-N 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- DTBHRRDGLARWLZ-UHFFFAOYSA-N 2-Methylbenzyl radical Chemical group [CH2]C1=CC=CC=C1C DTBHRRDGLARWLZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006487 butyl benzyl group Chemical group 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 29
- 238000002844 melting Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 230000000767 anti-ulcer Effects 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000875 corresponding Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960005141 piperazine Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MXHXXJOHFRHBFB-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanol Chemical compound CC1=CC=CC=C1C(O)C1=CC=CC=C1 MXHXXJOHFRHBFB-UHFFFAOYSA-N 0.000 description 1
- WGVYCXYGPNNUQA-UHFFFAOYSA-N 1-(bromomethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CBr WGVYCXYGPNNUQA-UHFFFAOYSA-N 0.000 description 1
- WHKWMTXTYKVFLK-UHFFFAOYSA-N 1-propan-2-ylpiperazine Chemical compound CC(C)N1CCNCC1 WHKWMTXTYKVFLK-UHFFFAOYSA-N 0.000 description 1
- LECMBPWEOVZHKN-UHFFFAOYSA-N 2-(2-chloroethoxy)ethanol Chemical compound OCCOCCCl LECMBPWEOVZHKN-UHFFFAOYSA-N 0.000 description 1
- JGDRELLAZGINQM-UHFFFAOYSA-N 2-Chlorobenzhydrol Chemical compound C=1C=CC=C(Cl)C=1C(O)C1=CC=CC=C1 JGDRELLAZGINQM-UHFFFAOYSA-N 0.000 description 1
- JNGIXKIMMGZPOG-UHFFFAOYSA-N 2-[4-[(3-methylphenyl)methyl]piperazin-1-yl]ethanol Chemical compound CC1=CC=CC(CN2CCN(CCO)CC2)=C1 JNGIXKIMMGZPOG-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N Bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- QILSFLSDHQAZET-UHFFFAOYSA-N Diphenylmethanol Chemical class C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- 206010013781 Dry mouth Diseases 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- 229960003506 PIPERAZINE HEXAHYDRATE Drugs 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001078 anti-cholinergic Effects 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 230000002005 ganglioplegic Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000020130 leben Nutrition 0.000 description 1
- AJYOOHCNOXWTKJ-UHFFFAOYSA-N p-Chlorobenzhydrol Chemical compound C=1C=C(Cl)C=CC=1C(O)C1=CC=CC=C1 AJYOOHCNOXWTKJ-UHFFFAOYSA-N 0.000 description 1
- 230000001734 parasympathetic Effects 0.000 description 1
- 230000003285 pharmacodynamic Effects 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 101710028591 sam1 Proteins 0.000 description 1
- 231100000486 side effect Toxicity 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 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)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE549420A true BE549420A (es) |
Family
ID=175658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE549420D BE549420A (es) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE549420A (es) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3238209A (en) * | 1961-02-22 | 1966-03-01 | Yoshitomi Pharmaceutical | (phenyl-methylthio)ethyl-piperazines and related compounds |
| DE1212091B (de) * | 1961-02-22 | 1966-03-10 | Yoshitomi Pharmaceutical | Verfahren zur Herstellung von Piperazinderivaten |
| FR2024775A1 (es) * | 1968-09-21 | 1970-09-04 | Boehringer Mannheim Gmbh | |
| US4874765A (en) * | 1986-04-22 | 1989-10-17 | Richter Gedeon Vegyeszeti Gyar | 1,4-Disubstituted piperazines having dopaminergic activity |
| JP2011144140A (ja) * | 2010-01-15 | 2011-07-28 | Tosoh Corp | Ｎ−（２，３−ジヒドロキシプロピル）ピペラジンの製造方法 |
-
0
- BE BE549420D patent/BE549420A/fr unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3238209A (en) * | 1961-02-22 | 1966-03-01 | Yoshitomi Pharmaceutical | (phenyl-methylthio)ethyl-piperazines and related compounds |
| DE1212091B (de) * | 1961-02-22 | 1966-03-10 | Yoshitomi Pharmaceutical | Verfahren zur Herstellung von Piperazinderivaten |
| FR2024775A1 (es) * | 1968-09-21 | 1970-09-04 | Boehringer Mannheim Gmbh | |
| US4874765A (en) * | 1986-04-22 | 1989-10-17 | Richter Gedeon Vegyeszeti Gyar | 1,4-Disubstituted piperazines having dopaminergic activity |
| JP2011144140A (ja) * | 2010-01-15 | 2011-07-28 | Tosoh Corp | Ｎ−（２，３−ジヒドロキシプロピル）ピペラジンの製造方法 |
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