CH651031A5 - Procede de preparation de (trialcoxy benzyl)-1 piperazines. - Google Patents
Procede de preparation de (trialcoxy benzyl)-1 piperazines. Download PDFInfo
- Publication number
- CH651031A5 CH651031A5 CH7061/81A CH706181A CH651031A5 CH 651031 A5 CH651031 A5 CH 651031A5 CH 7061/81 A CH7061/81 A CH 7061/81A CH 706181 A CH706181 A CH 706181A CH 651031 A5 CH651031 A5 CH 651031A5
- Authority
- CH
- Switzerland
- Prior art keywords
- benzyl
- piperazine
- piperazinone
- trimethoxy
- chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000004885 piperazines Chemical class 0.000 title claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 title 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 7
- -1 benzyl halide Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000004678 hydrides Chemical class 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 3
- HEAQHTKDZPKODU-UHFFFAOYSA-N 1-(chloromethyl)-2,3,4-trimethoxybenzene Chemical compound COC1=CC=C(CCl)C(OC)=C1OC HEAQHTKDZPKODU-UHFFFAOYSA-N 0.000 claims description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
- 229940073608 benzyl chloride Drugs 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- CRUILBNAQILVHZ-UHFFFAOYSA-N 1,2,3-trimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1OC CRUILBNAQILVHZ-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000007265 chloromethylation reaction Methods 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 229940030010 trimethoxybenzene Drugs 0.000 claims 1
- 125000001701 trimethoxybenzyl group Chemical group 0.000 claims 1
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 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
- 230000002908 adrenolytic effect Effects 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
- 125000001033 ether group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| CH651031A5 true CH651031A5 (fr) | 1985-08-30 |
Family
ID=9247720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7061/81A CH651031A5 (fr) | 1980-11-06 | 1981-11-04 | Procede de preparation de (trialcoxy benzyl)-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 |
| CA1181069A (fr) | 1985-01-15 |
| 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 |
| 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 |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |