FR2493316A1 - Nouveau procede de preparation des (trialcoxy benzyl)-1 piperazines et notamment de la (trimethoxy-2', 3', 4' benzyl)-1 piperazine - Google Patents
Nouveau procede de preparation des (trialcoxy benzyl)-1 piperazines et notamment de la (trimethoxy-2', 3', 4' benzyl)-1 piperazine Download PDFInfo
- Publication number
- FR2493316A1 FR2493316A1 FR8023678A FR8023678A FR2493316A1 FR 2493316 A1 FR2493316 A1 FR 2493316A1 FR 8023678 A FR8023678 A FR 8023678A FR 8023678 A FR8023678 A FR 8023678A FR 2493316 A1 FR2493316 A1 FR 2493316A1
- Authority
- FR
- France
- Prior art keywords
- benzyl
- piperazine
- piperazinone
- trimethoxy
- preparation
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title claims description 38
- 150000004885 piperazines Chemical class 0.000 title abstract description 5
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 7
- 150000004678 hydrides Chemical class 0.000 claims description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 4
- 229940073608 benzyl chloride Drugs 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 229910010084 LiAlH4 Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- CRUILBNAQILVHZ-UHFFFAOYSA-N 1,2,3-trimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1OC CRUILBNAQILVHZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 1
- UHWVSEOVJBQKBE-UHFFFAOYSA-N Trimetazidine Chemical compound COC1=C(OC)C(OC)=CC=C1CN1CCNCC1 UHWVSEOVJBQKBE-UHFFFAOYSA-N 0.000 description 1
- 230000002908 adrenolytic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- -1 for example Chemical compound 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000933 noradrenolytic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 description 1
- 235000019100 piperine Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000304 vasodilatating effect Effects 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)
Priority Applications (16)
| 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 |
| ES506814A ES8302679A1 (es) | 1980-11-06 | 1981-11-03 | Procedimiento de preparacion de una 1-(trialcoxibencil)pi- perazina. |
| MA19524A MA19322A1 (fr) | 1980-11-06 | 1981-11-03 | Procede de preparation de ( trialcoxybenzyl )- 1 piperazines |
| CH7061/81A CH651031A5 (fr) | 1980-11-06 | 1981-11-04 | Procede de preparation de (trialcoxy benzyl)-1 piperazines. |
| MX819743U MX6973E (es) | 1980-11-06 | 1981-11-04 | Procedimiento para preparar(trialcoxibencil)-1 piperazinas |
| IT49630/81A IT1142928B (it) | 1980-11-06 | 1981-11-04 | Procedimento per preparare i-(trialcossi-benzil)-piperazine |
| EG640/81A EG15454A (en) | 1980-11-06 | 1981-11-04 | Process for preparing of 1-(trialkoxybenzyl)piperazines |
| GR66443A GR75036B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-11-06 | 1981-11-05 | |
| AU77121/81A AU546225B2 (en) | 1980-11-06 | 1981-11-05 | Process for preparing 1-(trialkoxybenzyl)-piperazines |
| BE0/206459A BE891012A (fr) | 1980-11-06 | 1981-11-05 | Procede de preparation de (trialcoxy benzyl)-1 piperazines |
| CA000389487A CA1181069A (fr) | 1980-11-06 | 1981-11-05 | Procede de preparation de (trialcoxybenzyl)-1 piperazines |
| PT73935A PT73935B (fr) | 1980-11-06 | 1981-11-05 | Procede de preparation de (trialcoxybenzyl)-1 piperazines |
| LU83738A LU83738A1 (fr) | 1980-11-06 | 1981-11-05 | Procede de preparation de (trialcoxy benzyl)-1 piperazines |
| OA57535A OA06939A (fr) | 1980-11-06 | 1981-11-06 | Procédé de préparation de (trialcoxybenzyl)-1 pipérazines. |
| DE19813144235 DE3144235A1 (de) | 1980-11-06 | 1981-11-06 | Verfahren zur herstellung von 1-(trialkoxy-benzyl)-piperazinen |
| JP56178238A JPS57108086A (en) | 1980-11-06 | 1981-11-06 | Manufacture of 1-(trialkoxybenzyl)piperadine |
Applications Claiming Priority (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2493316A1 true FR2493316A1 (fr) | 1982-05-07 |
| FR2493316B1 FR2493316B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-04-15 |
Family
ID=9247720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8023678A Granted 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 |
Country Status (16)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0453365A1 (fr) * | 1990-04-20 | 1991-10-23 | Adir Et Compagnie | Procédé de préparation de la 1-(2,3,4-triméthoxybenzyl) pipérazine par amination réductive |
| EP0617027A1 (fr) * | 1993-03-24 | 1994-09-28 | Adir Et Compagnie | Nouveaux composés de N-benzylpipérazine leur procédé de préparation 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 |
Families Citing this family (2)
| 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. |
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2281764A1 (fr) * | 1974-08-12 | 1976-03-12 | Knoll Ag | Derives de la piperazine, leur procede de preparation et leur utilisation comme composes anti-arythmiques |
-
1980
- 1980-11-06 FR FR8023678A patent/FR2493316A1/fr active Granted
-
1981
- 1981-11-03 ES ES506814A patent/ES8302679A1/es not_active Expired
- 1981-11-03 MA MA19524A patent/MA19322A1/fr unknown
- 1981-11-04 CH CH7061/81A patent/CH651031A5/fr not_active IP Right Cessation
- 1981-11-04 IT IT49630/81A patent/IT1142928B/it active
- 1981-11-04 EG EG640/81A patent/EG15454A/xx active
- 1981-11-04 MX MX819743U patent/MX6973E/es unknown
- 1981-11-05 GR GR66443A patent/GR75036B/el unknown
- 1981-11-05 CA CA000389487A patent/CA1181069A/fr not_active Expired
- 1981-11-05 AU AU77121/81A patent/AU546225B2/en not_active Ceased
- 1981-11-05 LU LU83738A patent/LU83738A1/fr unknown
- 1981-11-05 PT PT73935A patent/PT73935B/pt unknown
- 1981-11-05 BE BE0/206459A patent/BE891012A/fr not_active IP Right Cessation
- 1981-11-06 JP JP56178238A patent/JPS57108086A/ja active Pending
- 1981-11-06 OA OA57535A patent/OA06939A/xx unknown
- 1981-11-06 DE DE19813144235 patent/DE3144235A1/de not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2281764A1 (fr) * | 1974-08-12 | 1976-03-12 | Knoll Ag | Derives de la piperazine, leur procede de preparation et leur utilisation comme composes anti-arythmiques |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0453365A1 (fr) * | 1990-04-20 | 1991-10-23 | Adir Et Compagnie | Procédé de préparation de la 1-(2,3,4-triméthoxybenzyl) pipérazine par amination réductive |
| FR2661176A1 (fr) * | 1990-04-20 | 1991-10-25 | Adir | Nouveau procede de preparation de la 1-(2,3,4-trimethoxybenzyl) piperazine en amination reductive. |
| US5142053A (en) * | 1990-04-20 | 1992-08-25 | Adir Et Compagnie | Process for the preparation of 1-(2,3,4-trimethoxybenzyl)piperazine by reductive animation |
| EP0617027A1 (fr) * | 1993-03-24 | 1994-09-28 | Adir Et Compagnie | Nouveaux composés de N-benzylpipérazine leur procédé de préparation et les compositions pharmaceutiques les renfermant |
| FR2703048A1 (fr) * | 1993-03-24 | 1994-09-30 | Adir | Nouveaux composés N-Benzylpiperazine, leur procédé de préparation 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| LU83738A1 (fr) | 1982-06-30 |
| EG15454A (en) | 1985-12-31 |
| OA06939A (fr) | 1983-07-31 |
| MA19322A1 (fr) | 1982-07-01 |
| CA1181069A (fr) | 1985-01-15 |
| CH651031A5 (fr) | 1985-08-30 |
| PT73935A (fr) | 1981-12-01 |
| IT1142928B (it) | 1986-10-15 |
| AU7712181A (en) | 1982-05-13 |
| ES506814A0 (es) | 1983-02-01 |
| BE891012A (fr) | 1982-05-05 |
| FR2493316B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-04-15 |
| JPS57108086A (en) | 1982-07-05 |
| ES8302679A1 (es) | 1983-02-01 |
| DE3144235A1 (de) | 1982-06-24 |
| GR75036B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-07-12 |
| AU546225B2 (en) | 1985-08-22 |
| PT73935B (fr) | 1983-11-30 |
| MX6973E (es) | 1987-01-13 |
| IT8149630A0 (it) | 1981-11-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |