CA1181069A - Procede de preparation de (trialcoxybenzyl)-1 piperazines - Google Patents
Procede de preparation de (trialcoxybenzyl)-1 piperazinesInfo
- Publication number
- CA1181069A CA1181069A CA000389487A CA389487A CA1181069A CA 1181069 A CA1181069 A CA 1181069A CA 000389487 A CA000389487 A CA 000389487A CA 389487 A CA389487 A CA 389487A CA 1181069 A CA1181069 A CA 1181069A
- Authority
- CA
- Canada
- Prior art keywords
- piperazinone
- benzyl
- phase
- solvent
- piperazine
- 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
- 150000004885 piperazines Chemical class 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000004678 hydrides Chemical class 0.000 claims abstract description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 7
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000003944 tolyl group Chemical group 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 7
- -1 2,3,4-trimethoxy benzyl Chemical group 0.000 abstract description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract description 2
- 229940073608 benzyl chloride Drugs 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HEAQHTKDZPKODU-UHFFFAOYSA-N 1-(chloromethyl)-2,3,4-trimethoxybenzene Chemical compound COC1=CC=C(CCl)C(OC)=C1OC HEAQHTKDZPKODU-UHFFFAOYSA-N 0.000 description 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 230000002908 adrenolytic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 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
- C07D295/096—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8023678A FR2493316A1 (fr) | 1980-11-06 | 1980-11-06 | Nouveau procede de preparation des (trialcoxy benzyl)-1 piperazines et notamment de la (trimethoxy-2', 3', 4' benzyl)-1 piperazine |
| FR80.23678 | 1980-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1181069A true CA1181069A (fr) | 1985-01-15 |
Family
ID=9247720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000389487A Expired CA1181069A (fr) | 1980-11-06 | 1981-11-05 | Procede de preparation de (trialcoxybenzyl)-1 piperazines |
Country Status (16)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH650176A5 (fr) * | 1982-08-23 | 1985-07-15 | Daussan & Co | Dispositif pour la coulee du metal fondu. |
| FR2661176B1 (fr) * | 1990-04-20 | 1992-06-12 | Adir | Nouveau procede de preparation de la 1-(2,3,4-trimethoxybenzyl) piperazine en amination reductive. |
| FR2703048B1 (fr) * | 1993-03-24 | 1996-01-05 | Adir | Nouveaux composes n-benzylpiperazine, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
| CN100413854C (zh) * | 2004-06-29 | 2008-08-27 | 北京德众万全药物技术开发有限公司 | 一种曲美他嗪及其药用盐的制备方法 |
| CN102993122B (zh) * | 2012-12-24 | 2015-03-04 | 武汉武药制药有限公司 | 盐酸曲美他嗪的合成新路线 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2438725A1 (de) * | 1974-08-12 | 1976-02-26 | Knoll Ag | Piperazinderivate |
-
1980
- 1980-11-06 FR FR8023678A patent/FR2493316A1/fr active Granted
-
1981
- 1981-11-03 MA MA19524A patent/MA19322A1/fr unknown
- 1981-11-03 ES ES506814A patent/ES506814A0/es active Granted
- 1981-11-04 CH CH7061/81A patent/CH651031A5/fr not_active IP Right Cessation
- 1981-11-04 MX MX819743U patent/MX6973E/es unknown
- 1981-11-04 IT IT49630/81A patent/IT1142928B/it active
- 1981-11-04 EG EG640/81A patent/EG15454A/xx active
- 1981-11-05 PT PT73935A patent/PT73935B/pt unknown
- 1981-11-05 CA CA000389487A patent/CA1181069A/fr not_active Expired
- 1981-11-05 LU LU83738A patent/LU83738A1/fr unknown
- 1981-11-05 BE BE0/206459A patent/BE891012A/fr not_active IP Right Cessation
- 1981-11-05 AU AU77121/81A patent/AU546225B2/en not_active Ceased
- 1981-11-05 GR GR66443A patent/GR75036B/el unknown
- 1981-11-06 JP JP56178238A patent/JPS57108086A/ja active Pending
- 1981-11-06 DE DE19813144235 patent/DE3144235A1/de not_active Withdrawn
- 1981-11-06 OA OA57535A patent/OA06939A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8302679A1 (es) | 1983-02-01 |
| PT73935B (fr) | 1983-11-30 |
| ES506814A0 (es) | 1983-02-01 |
| PT73935A (fr) | 1981-12-01 |
| OA06939A (fr) | 1983-07-31 |
| IT1142928B (it) | 1986-10-15 |
| MA19322A1 (fr) | 1982-07-01 |
| LU83738A1 (fr) | 1982-06-30 |
| FR2493316A1 (fr) | 1982-05-07 |
| AU546225B2 (en) | 1985-08-22 |
| GR75036B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-07-12 |
| CH651031A5 (fr) | 1985-08-30 |
| MX6973E (es) | 1987-01-13 |
| FR2493316B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-04-15 |
| DE3144235A1 (de) | 1982-06-24 |
| IT8149630A0 (it) | 1981-11-04 |
| EG15454A (en) | 1985-12-31 |
| BE891012A (fr) | 1982-05-05 |
| JPS57108086A (en) | 1982-07-05 |
| AU7712181A (en) | 1982-05-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |