CA1061343A - Substituted n-(1-(3,4-methylendioxyphenyl)-propyl(2))-n'-substituted phenylpiperazines - Google Patents
Substituted n-(1-(3,4-methylendioxyphenyl)-propyl(2))-n'-substituted phenylpiperazinesInfo
- Publication number
- CA1061343A CA1061343A CA234,707A CA234707A CA1061343A CA 1061343 A CA1061343 A CA 1061343A CA 234707 A CA234707 A CA 234707A CA 1061343 A CA1061343 A CA 1061343A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- group
- methylenedioxyphenyl
- prop
- 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
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 238000000034 method Methods 0.000 claims abstract description 43
- 239000002253 acid Substances 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- -1 1-(3,4-methylenedioxyphenyl)prop-2-yl compound Chemical class 0.000 claims description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052987 metal hydride Inorganic materials 0.000 claims description 7
- 150000004681 metal hydrides Chemical class 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- XIYKRJLTYKUWAM-UHFFFAOYSA-N 3,4-methylenedioxyphenylpropan-2-one Chemical compound CC(=O)CC1=CC=C2OCOC2=C1 XIYKRJLTYKUWAM-UHFFFAOYSA-N 0.000 claims description 2
- NOSSPDHLBXXMRA-UHFFFAOYSA-N 5-(2-chloropropyl)-1,3-benzodioxole Chemical compound CC(Cl)CC1=CC=C2OCOC2=C1 NOSSPDHLBXXMRA-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 17
- 239000012458 free base Substances 0.000 claims 3
- 238000006722 reduction reaction Methods 0.000 claims 3
- XEEABZILHXIMKD-UHFFFAOYSA-N 1-[1-(1,3-benzodioxol-5-yl)propan-2-yl]-4-(2,4-dichlorophenyl)piperazine Chemical compound C1OC=2C=C(C=CC2O1)CC(C)N1CCN(CC1)C1=C(C=C(C=C1)Cl)Cl XEEABZILHXIMKD-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- RVMKZYKJYMJYDG-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)propan-2-ol Chemical compound CC(O)CC1=CC=C2OCOC2=C1 RVMKZYKJYMJYDG-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- XGUJHSSIVVYJNU-UHFFFAOYSA-N CS(=O)(=O)OC(CC1=CC2=C(C=C1)OCO2)C Chemical compound CS(=O)(=O)OC(CC1=CC2=C(C=C1)OCO2)C XGUJHSSIVVYJNU-UHFFFAOYSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 7
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 3
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- YSJHCQGGIPTMQM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)piperazine Chemical compound ClC1=CC(Cl)=CC=C1N1CCNCC1 YSJHCQGGIPTMQM-UHFFFAOYSA-N 0.000 description 1
- QACLELNFVSMAIZ-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)piperazine Chemical compound CC1=CC(OC)=CC=C1N1CCNCC1 QACLELNFVSMAIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
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- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2442158A DE2442158C3 (de) | 1974-09-03 | 1974-09-03 | Neue substituierte N- [1(3,4-Methylendioxyphenyl) propyl (2)] -N'-subst Phenylpiperazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1061343A true CA1061343A (en) | 1979-08-28 |
Family
ID=5924765
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA234,708A Expired CA1063027A (en) | 1974-09-03 | 1975-09-03 | Substituted n-(1-(3,4-methylendioxyphenyl)-propyl(2))-n'-substituted phenylpiperazines |
| CA234,707A Expired CA1061343A (en) | 1974-09-03 | 1975-09-03 | Substituted n-(1-(3,4-methylendioxyphenyl)-propyl(2))-n'-substituted phenylpiperazines |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA234,708A Expired CA1063027A (en) | 1974-09-03 | 1975-09-03 | Substituted n-(1-(3,4-methylendioxyphenyl)-propyl(2))-n'-substituted phenylpiperazines |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS52287A (xx) |
| AT (1) | AT344699B (xx) |
| BE (2) | BE833002A (xx) |
| BG (1) | BG26381A3 (xx) |
| CA (2) | CA1063027A (xx) |
| CH (1) | CH615174A5 (xx) |
| CS (1) | CS192521B2 (xx) |
| DD (1) | DD124118A5 (xx) |
| DE (1) | DE2442158C3 (xx) |
| DK (1) | DK137387C (xx) |
| ES (5) | ES440630A1 (xx) |
| FI (1) | FI60006C (xx) |
| FR (1) | FR2283682A1 (xx) |
| GB (3) | GB1521052A (xx) |
| HU (1) | HU176754B (xx) |
| IE (2) | IE41667B1 (xx) |
| IL (2) | IL48033A (xx) |
| LU (2) | LU73316A1 (xx) |
| NL (1) | NL7510319A (xx) |
| NO (1) | NO142911C (xx) |
| NZ (1) | NZ178566A (xx) |
| PH (1) | PH13631A (xx) |
| PL (1) | PL95233B1 (xx) |
| RO (1) | RO68380B (xx) |
| SE (1) | SE419084B (xx) |
| YU (1) | YU37164B (xx) |
| ZA (2) | ZA755601B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54109307U (xx) * | 1978-01-19 | 1979-08-01 | ||
| US4647606A (en) * | 1982-12-27 | 1987-03-03 | Owens-Corning Fiberglas Corporation | Blend of rapid set asphaltic emulsion with slow set asphalt emulsion |
| HU187229B (en) * | 1983-04-14 | 1985-11-28 | Koezponti Valto Hitelbank | Method for producing fodder increasing yield or additional fodder composition |
| AUPN359095A0 (en) * | 1995-06-19 | 1995-07-13 | Mount Shamrock Pty Ltd | Saw system |
-
1974
- 1974-09-03 DE DE2442158A patent/DE2442158C3/de not_active Expired
-
1975
- 1975-08-13 FI FI752288A patent/FI60006C/fi not_active IP Right Cessation
- 1975-08-25 AT AT653875A patent/AT344699B/de not_active IP Right Cessation
- 1975-08-28 RO RO83281A patent/RO68380B/ro unknown
- 1975-09-01 BG BG030900A patent/BG26381A3/xx unknown
- 1975-09-01 CS CS755930A patent/CS192521B2/cs unknown
- 1975-09-01 DD DD188118A patent/DD124118A5/xx unknown
- 1975-09-02 GB GB3218/78A patent/GB1521052A/en not_active Expired
- 1975-09-02 GB GB36147/75A patent/GB1521051A/en not_active Expired
- 1975-09-02 BE BE159686A patent/BE833002A/xx not_active IP Right Cessation
- 1975-09-02 PL PL1975183066A patent/PL95233B1/pl unknown
- 1975-09-02 IL IL48033A patent/IL48033A/xx unknown
- 1975-09-02 HU HU75BO1570A patent/HU176754B/hu unknown
- 1975-09-02 DK DK393775A patent/DK137387C/da active
- 1975-09-02 IL IL48036A patent/IL48036A/xx unknown
- 1975-09-02 NL NL7510319A patent/NL7510319A/xx not_active Application Discontinuation
- 1975-09-02 ES ES440630A patent/ES440630A1/es not_active Expired
- 1975-09-02 JP JP50106441A patent/JPS52287A/ja active Pending
- 1975-09-02 SE SE7509746A patent/SE419084B/xx unknown
- 1975-09-02 YU YU2219/75A patent/YU37164B/xx unknown
- 1975-09-02 GB GB36152/75A patent/GB1514546A/en not_active Expired
- 1975-09-02 NO NO753020A patent/NO142911C/no unknown
- 1975-09-02 BE BE159687A patent/BE833003A/xx not_active IP Right Cessation
- 1975-09-03 ZA ZA755601A patent/ZA755601B/xx unknown
- 1975-09-03 PH PH17540A patent/PH13631A/en unknown
- 1975-09-03 ZA ZA755602A patent/ZA755602B/xx unknown
- 1975-09-03 LU LU73316A patent/LU73316A1/xx unknown
- 1975-09-03 IE IE1929/75A patent/IE41667B1/en unknown
- 1975-09-03 CA CA234,708A patent/CA1063027A/en not_active Expired
- 1975-09-03 IE IE1930/75A patent/IE43338B1/en unknown
- 1975-09-03 NZ NZ178566A patent/NZ178566A/xx unknown
- 1975-09-03 LU LU73317A patent/LU73317A1/xx unknown
- 1975-09-03 FR FR7527056A patent/FR2283682A1/fr active Granted
- 1975-09-03 CA CA234,707A patent/CA1061343A/en not_active Expired
-
1976
- 1976-12-03 ES ES453932A patent/ES453932A1/es not_active Expired
- 1976-12-03 ES ES453934A patent/ES453934A1/es not_active Expired
- 1976-12-03 ES ES453935A patent/ES453935A1/es not_active Expired
- 1976-12-03 ES ES453933A patent/ES453933A1/es not_active Expired
-
1979
- 1979-05-07 CH CH425779A patent/CH615174A5/de not_active IP Right Cessation
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