LU83738A1 - Procede de preparation de (trialcoxy benzyl)-1 piperazines - Google Patents
Procede de preparation de (trialcoxy benzyl)-1 piperazines Download PDFInfo
- Publication number
- LU83738A1 LU83738A1 LU83738A LU83738A LU83738A1 LU 83738 A1 LU83738 A1 LU 83738A1 LU 83738 A LU83738 A LU 83738A LU 83738 A LU83738 A LU 83738A LU 83738 A1 LU83738 A1 LU 83738A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- benzyl
- piperazine
- piperazinone
- trimethoxy
- phase
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000004885 piperazines Chemical class 0.000 title description 4
- 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 34
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 150000004678 hydrides Chemical class 0.000 claims description 6
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- -1 alkoxy benzoic acid Chemical compound 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
- 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
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 230000002908 adrenolytic effect Effects 0.000 description 1
- 125000001931 aliphatic 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
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 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
- 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
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001701 trimethoxybenzyl group Chemical group 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8023678 | 1980-11-06 | ||
| 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 |
|---|---|
| LU83738A1 true LU83738A1 (fr) | 1982-06-30 |
Family
ID=9247720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU83738A LU83738A1 (fr) | 1980-11-06 | 1981-11-05 | Procede de preparation de (trialcoxy benzyl)-1 piperazines |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS57108086A (en, 2012) |
| AU (1) | AU546225B2 (en, 2012) |
| BE (1) | BE891012A (en, 2012) |
| CA (1) | CA1181069A (en, 2012) |
| CH (1) | CH651031A5 (en, 2012) |
| DE (1) | DE3144235A1 (en, 2012) |
| EG (1) | EG15454A (en, 2012) |
| ES (1) | ES506814A0 (en, 2012) |
| FR (1) | FR2493316A1 (en, 2012) |
| GR (1) | GR75036B (en, 2012) |
| IT (1) | IT1142928B (en, 2012) |
| LU (1) | LU83738A1 (en, 2012) |
| MA (1) | MA19322A1 (en, 2012) |
| MX (1) | MX6973E (en, 2012) |
| OA (1) | OA06939A (en, 2012) |
| PT (1) | PT73935B (en, 2012) |
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 IT IT49630/81A patent/IT1142928B/it active
- 1981-11-04 CH CH7061/81A patent/CH651031A5/fr not_active IP Right Cessation
- 1981-11-04 EG EG640/81A patent/EG15454A/xx active
- 1981-11-04 MX MX819743U patent/MX6973E/es unknown
- 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 CA CA000389487A patent/CA1181069A/fr not_active Expired
- 1981-11-05 GR GR66443A patent/GR75036B/el unknown
- 1981-11-05 PT PT73935A patent/PT73935B/pt unknown
- 1981-11-05 AU AU77121/81A patent/AU546225B2/en not_active Ceased
- 1981-11-06 DE DE19813144235 patent/DE3144235A1/de not_active Withdrawn
- 1981-11-06 OA OA57535A patent/OA06939A/xx unknown
- 1981-11-06 JP JP56178238A patent/JPS57108086A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1142928B (it) | 1986-10-15 |
| MA19322A1 (fr) | 1982-07-01 |
| MX6973E (es) | 1987-01-13 |
| EG15454A (en) | 1985-12-31 |
| ES8302679A1 (es) | 1983-02-01 |
| AU546225B2 (en) | 1985-08-22 |
| DE3144235A1 (de) | 1982-06-24 |
| FR2493316B1 (en, 2012) | 1983-04-15 |
| JPS57108086A (en) | 1982-07-05 |
| PT73935A (fr) | 1981-12-01 |
| OA06939A (fr) | 1983-07-31 |
| IT8149630A0 (it) | 1981-11-04 |
| CA1181069A (fr) | 1985-01-15 |
| AU7712181A (en) | 1982-05-13 |
| PT73935B (fr) | 1983-11-30 |
| CH651031A5 (fr) | 1985-08-30 |
| FR2493316A1 (fr) | 1982-05-07 |
| ES506814A0 (es) | 1983-02-01 |
| BE891012A (fr) | 1982-05-05 |
| GR75036B (en, 2012) | 1984-07-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0430771B1 (fr) | Dérivés de l'isoindolone, leur préparation et leur utilisation comme intermédiaires pour la préparation d'antagonistes de la substance P | |
| JPS63196554A (ja) | Ｎ−アルキル−ｎ’−メチル−アルキレン尿素、特にｎ，ｎ’−ジメチルアルキレン尿素の製造方法 | |
| FR2590255A1 (fr) | Procede de preparation de derives de la pteridine | |
| LU83738A1 (fr) | Procede de preparation de (trialcoxy benzyl)-1 piperazines | |
| CH479552A (fr) | Procédé pour la préparation de cétimines | |
| CA1091673A (en) | Diamino-benzylpyrimidines | |
| RU2007402C1 (ru) | Способ получения производных 2-азабицикло(2,2,1)гепт-5-ен-2-уксусной кислоты | |
| EP0053949B1 (fr) | Procédé nouveau de préparation des tétrahydro-5,6,7,7a-4H-thiéno(3,2-c)pyridinones-2 | |
| JP3223377B2 (ja) | 対称的な２，２’−メチレンビスベンゾトリアゾリル フェノール類の製造方法 | |
| KR100293646B1 (ko) | 해당알독심의탈수반응을통하여오르토-하이드록시치환된방향족니트릴을제조하는방법 | |
| US5756724A (en) | High-yielding ullmann reaction for the preparation of bipyrroles | |
| Kinoshita et al. | Synthesis of 2-(substituted Methyl)-3, 4-Disubstituted Pyrroles and Their Conversion into the Corresponding Porphyrins. | |
| JPH062747B2 (ja) | ２‐アルキル‐４，５‐ジヒドロキシメチルイミダゾールの製法 | |
| US5910594A (en) | Process for the manufacture of 5-cyano-4-lower alkyl-oxazoles | |
| RU2116299C1 (ru) | Способ получения 2-замещенных 5-хлоримидазол-4-карбальдегидов и 2-замещенный 3,5-дигидроимидазолин-4-он | |
| CA2007718A1 (fr) | Procede de separation d'isomeres optiques des derives de la dihydro-1,4 pyridine | |
| JP2622747B2 (ja) | シス―７―デセン―４―オリドの製造方法 | |
| KR900005255B1 (ko) | N-[3-[3-(1-피페리디닐메틸)페녹시]프로필]아세톡시아세트아미드 염산염의 제조방법 | |
| BE879730R (fr) | Derives d'alkylenediamines | |
| FR2681323A1 (fr) | Nouveau derive de l'amino-2 imidazole, sa preparation et son emploi. | |
| KR950013853B1 (ko) | 4-에톡시카보닐-i-메틸-5-피라졸머캅탄의 제조방법 | |
| JPH06102636B2 (ja) | Ｎ―メチル―３，４―ジメトキシフェニルエチルアミンの新規合成方法 | |
| EP0215477A1 (en) | Process and intermediates for antiarrhytmic 1,3-diazabicyclo/4.4.0/dec-2-en-4-ones | |
| FR2600333A1 (fr) | Procede pour la preparation de 4-alcoxy-3-pyrroline-2-ones | |
| US4454351A (en) | Lactonic derivatives and use of same as starting materials for the preparation of macrocyclic hydroxyketones |