ES395969A1 - Neuroleptic 1-aralkyl-4-phenyl-piperazines prodn - by reacting ethylenediamines with oxalic acid derivs,and reducing resulting dioxo - Google Patents
Neuroleptic 1-aralkyl-4-phenyl-piperazines prodn - by reacting ethylenediamines with oxalic acid derivs,and reducing resulting dioxoInfo
- Publication number
- ES395969A1 ES395969A1 ES395969A ES395969A ES395969A1 ES 395969 A1 ES395969 A1 ES 395969A1 ES 395969 A ES395969 A ES 395969A ES 395969 A ES395969 A ES 395969A ES 395969 A1 ES395969 A1 ES 395969A1
- Authority
- ES
- Spain
- Prior art keywords
- piperazines
- dioxo
- aralkyl
- phenyl
- neuroleptic
- 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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 title 3
- 150000002171 ethylene diamines Chemical class 0.000 title 1
- 239000003176 neuroleptic agent Substances 0.000 title 1
- 230000000701 neuroleptic effect Effects 0.000 title 1
- 235000006408 oxalic acid Nutrition 0.000 title 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- 229910010084 LiAlH4 Inorganic materials 0.000 abstract 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 229940012017 ethylenediamine Drugs 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- JTHRRMFZHSDGNJ-UHFFFAOYSA-N piperazine-2,3-dione Chemical compound O=C1NCCNC1=O JTHRRMFZHSDGNJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000013570 smoothie Nutrition 0.000 abstract 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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)
Abstract
Title 1-aralkyl-4-phenyl-piperazines of formula (I): (where Ar is an aromatic residue with 2 fused rings of which the one not linked to the rest of the molecule may be an iso- or heterocyclic satd. or aromatic ring, and R1 and R2 are H, halogen, amino, acylamino, CN, CF3 or 1-4C alkyl, alkoxy, alkylcarbonyl or alkylthio) are prepd. by reacting an ethylene-diamine deriv. of formula (II): with a cpd. X-CO-CO-X (where X is halogen or lower alkoxy) and reducing the resulting dioxo-piperazine cpd. (III): with metal hydrides (e.g. LiAlH4, sodium bis-(2-methoxyethoxy)-aluminium hydride or diborane). (I) thus obtained may be converted into a physiologically tolerable acid addn. salt. The process uses very readily available starting materials and proceeds smoothy and with good yields sterically hindered products are easily produced.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19702050684 DE2050684A1 (en) | 1970-10-15 | 1970-10-15 | Neuroleptic 1-aralkyl-4-phenyl-piperazines prodn - by reacting ethylenediamines with oxalic acid derivs,and reducing resulting dioxo |
Publications (1)
Publication Number | Publication Date |
---|---|
ES395969A1 true ES395969A1 (en) | 1973-12-16 |
Family
ID=5785239
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES395969A Expired ES395969A1 (en) | 1970-10-15 | 1971-10-14 | Neuroleptic 1-aralkyl-4-phenyl-piperazines prodn - by reacting ethylenediamines with oxalic acid derivs,and reducing resulting dioxo |
Country Status (12)
Country | Link |
---|---|
AT (1) | AT313902B (en) |
BG (1) | BG18869A3 (en) |
CA (1) | CA967159A (en) |
CH (1) | CH562236A5 (en) |
DE (1) | DE2050684A1 (en) |
DK (1) | DK142580C (en) |
ES (1) | ES395969A1 (en) |
FI (1) | FI54922C (en) |
HU (1) | HU162740B (en) |
PL (1) | PL77016B1 (en) |
SE (1) | SE395144B (en) |
YU (1) | YU34695B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2604838A1 (en) * | 1976-02-07 | 1977-08-11 | Knoll Ag | ALKYLENE DIOXYPIPERAZINE DERIVATIVES |
-
1970
- 1970-10-15 DE DE19702050684 patent/DE2050684A1/en active Pending
-
1971
- 1971-10-12 CH CH1491871A patent/CH562236A5/xx not_active IP Right Cessation
- 1971-10-12 HU HUBO1323A patent/HU162740B/hu unknown
- 1971-10-13 BG BG18756A patent/BG18869A3/xx unknown
- 1971-10-13 SE SE7112983A patent/SE395144B/en unknown
- 1971-10-14 PL PL1971151024A patent/PL77016B1/pl unknown
- 1971-10-14 CA CA125,116A patent/CA967159A/en not_active Expired
- 1971-10-14 FI FI2885/71A patent/FI54922C/en active
- 1971-10-14 ES ES395969A patent/ES395969A1/en not_active Expired
- 1971-10-14 AT AT890171A patent/AT313902B/en not_active IP Right Cessation
- 1971-10-15 YU YU2633/71A patent/YU34695B/en unknown
- 1971-10-15 DK DK503071A patent/DK142580C/en active
Also Published As
Publication number | Publication date |
---|---|
PL77016B1 (en) | 1975-02-28 |
HU162740B (en) | 1973-04-28 |
AT313902B (en) | 1974-03-11 |
DK142580B (en) | 1980-11-24 |
BG18869A3 (en) | 1975-03-20 |
YU263371A (en) | 1979-07-10 |
FI54922C (en) | 1979-04-10 |
DK142580C (en) | 1981-07-13 |
DE2050684A1 (en) | 1972-04-20 |
CA967159A (en) | 1975-05-06 |
YU34695B (en) | 1979-12-31 |
CH562236A5 (en) | 1975-05-30 |
FI54922B (en) | 1978-12-29 |
SE395144B (en) | 1977-08-01 |
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