GB1171251A - Preparation of Piperazine Derivatives - Google Patents
Preparation of Piperazine DerivativesInfo
- Publication number
- GB1171251A GB1171251A GB30873/67A GB3087367A GB1171251A GB 1171251 A GB1171251 A GB 1171251A GB 30873/67 A GB30873/67 A GB 30873/67A GB 3087367 A GB3087367 A GB 3087367A GB 1171251 A GB1171251 A GB 1171251A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- chloro
- piperazine
- carbon atoms
- reacting
- 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
- 150000004885 piperazines Chemical class 0.000 title abstract 5
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract 3
- -1 2-hydroxycyclohexyl Chemical group 0.000 abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- NLIZRQRMTSWKNN-UHFFFAOYSA-N 1-bromo-4-(2-ethylbutyl)benzene Chemical compound CCC(CC)CC1=CC=C(Br)C=C1 NLIZRQRMTSWKNN-UHFFFAOYSA-N 0.000 abstract 2
- MXHOLIARBWJKCR-UHFFFAOYSA-N 1-bromo-4-hexylbenzene Chemical compound CCCCCCC1=CC=C(Br)C=C1 MXHOLIARBWJKCR-UHFFFAOYSA-N 0.000 abstract 2
- FWNXUYJSLXBPRJ-UHFFFAOYSA-N 1-chloro-3-(4-cyclohexylphenyl)propan-2-ol Chemical compound C1=CC(CC(CCl)O)=CC=C1C1CCCCC1 FWNXUYJSLXBPRJ-UHFFFAOYSA-N 0.000 abstract 2
- VBGMXLDNALYYHE-UHFFFAOYSA-N 2-bromo-1-butoxy-4-cyclohexylbenzene Chemical compound C(CCC)OC1=C(C=C(C=C1)C1CCCCC1)Br VBGMXLDNALYYHE-UHFFFAOYSA-N 0.000 abstract 2
- DSYPBKQKCSJRHB-UHFFFAOYSA-N 2-bromo-4-cyclohexylphenol Chemical compound C1=C(Br)C(O)=CC=C1C1CCCCC1 DSYPBKQKCSJRHB-UHFFFAOYSA-N 0.000 abstract 2
- YMDZDFSUDFLGMX-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)ethanamine;hydron;chloride Chemical compound [Cl-].ClCC[NH2+]CCCl YMDZDFSUDFLGMX-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 abstract 1
- HJBXDGLSLSGHRV-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)piperazine;hydrochloride Chemical compound Cl.COC1=CC(OC)=CC=C1N1CCNCC1 HJBXDGLSLSGHRV-UHFFFAOYSA-N 0.000 abstract 1
- XYHXYXXVKQCEIC-UHFFFAOYSA-N 1-(4-chloro-2-nitrophenyl)piperazine;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC(Cl)=CC=C1N1CCNCC1 XYHXYXXVKQCEIC-UHFFFAOYSA-N 0.000 abstract 1
- NTLFAHFTZBIIPG-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)piperazine;hydrochloride Chemical compound [Cl-].COC1=CC=C(Cl)C=C1N1CC[NH2+]CC1 NTLFAHFTZBIIPG-UHFFFAOYSA-N 0.000 abstract 1
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 abstract 1
- INEXSMKRMASIRN-UHFFFAOYSA-N 1-bromo-2-cyclohexyloxybenzene Chemical compound BrC1=CC=CC=C1OC1CCCCC1 INEXSMKRMASIRN-UHFFFAOYSA-N 0.000 abstract 1
- JPMJVIPNEVCQFQ-UHFFFAOYSA-N 1-chloro-3-[4-(2-ethylbutyl)phenyl]propan-2-ol Chemical compound ClCC(CC1=CC=C(C=C1)CC(CC)CC)O JPMJVIPNEVCQFQ-UHFFFAOYSA-N 0.000 abstract 1
- GEQNZVKIDIPGCO-UHFFFAOYSA-N 2,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C(OC)=C1 GEQNZVKIDIPGCO-UHFFFAOYSA-N 0.000 abstract 1
- MOBNLCPBAMKACS-UHFFFAOYSA-N 2-(1-chloroethyl)oxirane Chemical compound CC(Cl)C1CO1 MOBNLCPBAMKACS-UHFFFAOYSA-N 0.000 abstract 1
- NUUBOMRATNSTIX-UHFFFAOYSA-N 2-[(4-cyclohexylphenyl)methyl]oxirane Chemical compound C=1C=C(C2CCCCC2)C=CC=1CC1CO1 NUUBOMRATNSTIX-UHFFFAOYSA-N 0.000 abstract 1
- IRTONKUCLPTRNS-UHFFFAOYSA-N 2-butoxyaniline Chemical compound CCCCOC1=CC=CC=C1N IRTONKUCLPTRNS-UHFFFAOYSA-N 0.000 abstract 1
- XLXKNHSGAGUAKZ-UHFFFAOYSA-N 2-ethylbutylbenzene Chemical compound CCC(CC)CC1=CC=CC=C1 XLXKNHSGAGUAKZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 abstract 1
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 abstract 1
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002924 oxiranes Chemical class 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 238000010992 reflux Methods 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
- C07D295/04—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
- C07D295/06—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 halogen atoms or nitro radicals
- C07D295/073—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 halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- 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
- C07D295/084—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30873/67A GB1171251A (en) | 1967-07-05 | 1967-07-05 | Preparation of Piperazine Derivatives |
| IE734/68A IE32152B1 (en) | 1967-07-05 | 1968-06-20 | Preparation of piperazine derivatives |
| DK309268AA DK120998B (da) | 1967-07-05 | 1968-06-27 | Analogifremgangsmåde til fremstilling af piperazinderivater eller syreadditionssalte deraf. |
| NO682568A NO126082B (enrdf_load_stackoverflow) | 1967-07-05 | 1968-06-28 | |
| NL6809422A NL6809422A (enrdf_load_stackoverflow) | 1967-07-05 | 1968-07-03 | |
| AT639368A AT281038B (de) | 1967-07-05 | 1968-07-03 | Verfahren zur Herstellung von neuen Piperazinderivaten und ihren Salzen |
| IL30313A IL30313A (en) | 1967-07-05 | 1968-07-04 | Phenyl-(2-hydroxy)-propyl piperazine derivatives |
| ES355739A ES355739A1 (es) | 1967-07-05 | 1968-07-04 | Procedimiento para la preparacion de derivados de piperazi-na. |
| FR1583999D FR1583999A (enrdf_load_stackoverflow) | 1967-07-05 | 1968-07-04 | |
| CH1009968A CH496005A (de) | 1967-07-05 | 1968-07-05 | Verfahren zur Herstellung von Piperazin-Derivaten |
| SE09283/68A SE352891B (enrdf_load_stackoverflow) | 1967-07-05 | 1968-07-05 | |
| DE19681770805 DE1770805A1 (de) | 1967-07-05 | 1968-07-05 | Substituierte Piperazine und Verfahren zu ihrer Herstellung |
| US00156092A US3732229A (en) | 1967-07-05 | 1971-06-23 | 3-cyclohexyl phenyl-2-hydroxypropyl-4-phenyl piperazines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30873/67A GB1171251A (en) | 1967-07-05 | 1967-07-05 | Preparation of Piperazine Derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1171251A true GB1171251A (en) | 1969-11-19 |
Family
ID=10314465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30873/67A Expired GB1171251A (en) | 1967-07-05 | 1967-07-05 | Preparation of Piperazine Derivatives |
Country Status (13)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2277517A (en) * | 1993-04-27 | 1994-11-02 | Wyeth John & Brother Ltd | N-[(2-aryl-phenyl)alkyl]-piperazine derivatives |
| WO2001055111A1 (en) * | 2000-01-27 | 2001-08-02 | Ribotargets Limited | Biaryl compounds, their preparation and their use in therapy |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2081557B1 (enrdf_load_stackoverflow) * | 1970-03-02 | 1973-08-10 | Cerm Cent Europ Rech Mauvernay | |
| US3951978A (en) * | 1972-04-22 | 1976-04-20 | Istituto Luso Farmaco D'italia S.R.L. | 1,3-Disubstituted 3-aroylpropanes and process for the preparation thereof |
| DE2246279A1 (de) * | 1972-09-21 | 1974-05-22 | Goedecke Ag | Neue 1-aryl-2-arylalkyl-3-(4)-eckige klammer auf 4'-(subst.-alkyl)-piperazino1' eckige klammer zu -butanole-2 bzw. butene-1 und verfahren zu ihrer herstellung |
| JO2857B1 (en) * | 2008-06-16 | 2015-03-15 | سانوفي أفينتس | Vinyl pipers with modified activity of tumor-resistant TNF |
-
1967
- 1967-07-05 GB GB30873/67A patent/GB1171251A/en not_active Expired
-
1968
- 1968-06-20 IE IE734/68A patent/IE32152B1/xx unknown
- 1968-06-27 DK DK309268AA patent/DK120998B/da unknown
- 1968-06-28 NO NO682568A patent/NO126082B/no unknown
- 1968-07-03 NL NL6809422A patent/NL6809422A/xx unknown
- 1968-07-03 AT AT639368A patent/AT281038B/de not_active IP Right Cessation
- 1968-07-04 FR FR1583999D patent/FR1583999A/fr not_active Expired
- 1968-07-04 IL IL30313A patent/IL30313A/xx unknown
- 1968-07-04 ES ES355739A patent/ES355739A1/es not_active Expired
- 1968-07-05 CH CH1009968A patent/CH496005A/de not_active IP Right Cessation
- 1968-07-05 SE SE09283/68A patent/SE352891B/xx unknown
- 1968-07-05 DE DE19681770805 patent/DE1770805A1/de active Pending
-
1971
- 1971-06-23 US US00156092A patent/US3732229A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2277517A (en) * | 1993-04-27 | 1994-11-02 | Wyeth John & Brother Ltd | N-[(2-aryl-phenyl)alkyl]-piperazine derivatives |
| US5430033A (en) * | 1993-04-27 | 1995-07-04 | John Wyeth & Brother Ltd. | Piperazine derivatives |
| GB2277517B (en) * | 1993-04-27 | 1996-09-11 | Wyeth John & Brother Ltd | Piperazine derivatives |
| WO2001055111A1 (en) * | 2000-01-27 | 2001-08-02 | Ribotargets Limited | Biaryl compounds, their preparation and their use in therapy |
Also Published As
| Publication number | Publication date |
|---|---|
| DK120998B (da) | 1971-08-16 |
| CH496005A (de) | 1970-09-15 |
| IE32152B1 (en) | 1973-05-02 |
| ES355739A1 (es) | 1969-12-16 |
| NL6809422A (enrdf_load_stackoverflow) | 1969-01-07 |
| US3732229A (en) | 1973-05-08 |
| IL30313A0 (en) | 1968-09-26 |
| IL30313A (en) | 1972-08-30 |
| IE32152L (en) | 1969-01-05 |
| FR1583999A (enrdf_load_stackoverflow) | 1969-12-12 |
| SE352891B (enrdf_load_stackoverflow) | 1973-01-15 |
| NO126082B (enrdf_load_stackoverflow) | 1972-12-18 |
| AT281038B (de) | 1970-05-11 |
| DE1770805A1 (de) | 1972-01-13 |
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