GB1171251A - Preparation of Piperazine Derivatives - Google Patents

Preparation of Piperazine Derivatives

Info

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
Application number
GB30873/67A
Inventor
Peter Thomas Bysouth
Robert William Clarke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BDH Chemicals Ltd
Original Assignee
BDH Chemicals Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BDH Chemicals Ltd filed Critical BDH Chemicals Ltd
Priority to GB30873/67A priority Critical patent/GB1171251A/en
Priority to IE734/68A priority patent/IE32152B1/en
Priority to DK309268AA priority patent/DK120998B/en
Priority to NO682568A priority patent/NO126082B/no
Priority to AT639368A priority patent/AT281038B/en
Priority to NL6809422A priority patent/NL6809422A/xx
Priority to IL30313A priority patent/IL30313A/en
Priority to FR1583999D priority patent/FR1583999A/fr
Priority to ES355739A priority patent/ES355739A1/en
Priority to SE09283/68A priority patent/SE352891B/xx
Priority to CH1009968A priority patent/CH496005A/en
Priority to DE19681770805 priority patent/DE1770805A1/en
Publication of GB1171251A publication Critical patent/GB1171251A/en
Priority to US00156092A priority patent/US3732229A/en
Expired legal-status Critical Current

Links

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)

Abstract

1,171,251. Piperazine derivatives. BRITISH DRUG HOUSES Ltd. 19 June, 1968 [5 July, 1967], No. 30873/67. Heading C2C. Novel piperazine derivatives having the general formula where R = hydrogen or alkoxy (containing from 1-8 carbon atoms in a straight or branched chain). R<SP>1</SP> = alkyl, either straight or branched chain containing up to 10 carbon atoms; alkoxy, either straight or branched chain containing up to 10 carbon atoms; cycloalkyl containing from 5-7 carbon atoms; cycloalkyloxy containing from 5-7 carbon atoms; cyclo-alk-1-enyl containing from 5-7 carbon atoms; phenyl; phenoxy or halogen. R<SP>2</SP> = hydrogen or methyl; R<SP>3</SP> = 2-hydroxycyclohexyl; phenyl or mono-, di- or trisubstituted phenyl, or a 2-pyridyl nucleus; are prepared by reacting a chlorohydrin having the formula where R, R<SP>1</SP> and R<SP>2</SP> have the same meanings as above, and a base with a substituted piperazine having the formula where R<SP>3</SP> has the same meaning as above. The chlorohydrin may be reacted initially with the base to form the corresponding epoxide which is subsequently reacted with the substituted piperazine. 1 - (p - Biphenyl) and 1 - (p - cyclohexylphenyl) - 2,3 - epoxypropane are prepared by heating 1 - (p - biphenylyl) - 3 - chloro - and 1 - chloro - 3 - (p - cyclohexylphenyl) - propan- 2 - ol respectively, 1 - (p - bromophenyl)- hexane and 3 - (p - bromobenzyl) - pentane are prepared by adding bromine to 1-phenylhexane and 3-benzylpentane respectively in the presence of iron powder. 1-Chloro-3-(p-hexylphenyl), 1 - chloro - 3 - (2 - n - butoxy - 5 - cyclohexyl)- phenyl, 1 - chloro - 3 - (o - cyclohexyloxyphenyl) and 1 - chloro - 3 - [4 - (2 - ethylbutyl) - phenyl]- propan-2-ol are prepared by adding a solution of epichlorohydrin in ether to a Grignard reagent prepared from 1-(p-bromophenyl)-hexane, 2 - n - butoxy - 5 - cyclohexylbromobenzene, o - cyclohexyloxybromobenzene and 3-(p-bromobenzyl)-pentane respectively, ethyl bromide and magnesium. 1-(m-Bromophenyl) 1 - (o - ethoxyphenyl), 1 - (o - butoxyphenyl) and 1 - (2,4 - dimethoxyphenyl) - piperazine hydrochloride are prepared by reacting m-bromoaniline, o-phenetidine-, o-butoxy- and 2,4- dimethoxy-aniline respectively with bis-(2- chloroethyl) - amine hydrochloride. 1 - Chloro- 3 - (p - cyclohexylphenyl) - 2 - methyl and 1- chloro - 3 - (p - cyclohexylphenyl) - propan - 2 - ol are prepared by adding methylepichlorohydrin and epichlorohydrin respectively to a Grignard solution prepared from magnesium and pbromophenylcyclohexane. 2 - Bromo - 4 - cyclohexylphenol is prepared by reacting bromine with p-cyclohexylphenol. 2 - n - Butoxy - 5 - cyclohexylbromobenzene is prepared by reacting n - bromobutane and 2 - bromo - 4 - cyclohexylphenol. 1 - (4 - Chloro - 2 - nitrophenyl)- piperazine hydrochloride is prepared by refluxing piperazine and 2,5-dichloronitrobenzene. 1 - (5 - Chloro - 2 - methoxyphenyl) - piperazine hydrochloride is prepared by reacting bis-(2- chloroethyl) - amine hydrochloride and 5- chloro-2-methoxyaniline.
GB30873/67A 1967-07-05 1967-07-05 Preparation of Piperazine Derivatives Expired GB1171251A (en)

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 (en) 1967-07-05 1968-06-27 Analogous process for the preparation of piperazine derivatives or acid addition salts thereof.
NO682568A NO126082B (en) 1967-07-05 1968-06-28
AT639368A AT281038B (en) 1967-07-05 1968-07-03 Process for the preparation of new piperazine derivatives and their salts
NL6809422A NL6809422A (en) 1967-07-05 1968-07-03
FR1583999D FR1583999A (en) 1967-07-05 1968-07-04
IL30313A IL30313A (en) 1967-07-05 1968-07-04 Phenyl-(2-hydroxy)-propyl piperazine derivatives
ES355739A ES355739A1 (en) 1967-07-05 1968-07-04 3-cyclohexyl phenyl-2-hydroxypropyl-4-phenyl piperazines
SE09283/68A SE352891B (en) 1967-07-05 1968-07-05
CH1009968A CH496005A (en) 1967-07-05 1968-07-05 Process for the preparation of piperazine derivatives
DE19681770805 DE1770805A1 (en) 1967-07-05 1968-07-05 Substituted piperazines and processes for their preparation
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)

Country Link
US (1) US3732229A (en)
AT (1) AT281038B (en)
CH (1) CH496005A (en)
DE (1) DE1770805A1 (en)
DK (1) DK120998B (en)
ES (1) ES355739A1 (en)
FR (1) FR1583999A (en)
GB (1) GB1171251A (en)
IE (1) IE32152B1 (en)
IL (1) IL30313A (en)
NL (1) NL6809422A (en)
NO (1) NO126082B (en)
SE (1) SE352891B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2081557B1 (en) * 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 (en) * 1972-09-21 1974-05-22 Goedecke Ag NEW 1-ARYL-2-ARYLALKYL-3- (4) -ANGULAR CLAMP ON 4 '- (SUBST.-ALKYL) -PIPERAZINO1' ANGLE CLAMP FOR -BUTANOLE-2 OR. BUTENE-1 AND THE METHOD FOR MANUFACTURING IT
JO2857B1 (en) * 2008-06-16 2015-03-15 سانوفي أفينتس Phenyl-alkylpiperazines with tnf-modulating activity

Cited By (4)

* Cited by examiner, † Cited by third party
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
NO126082B (en) 1972-12-18
DK120998B (en) 1971-08-16
DE1770805A1 (en) 1972-01-13
AT281038B (en) 1970-05-11
ES355739A1 (en) 1969-12-16
IE32152B1 (en) 1973-05-02
FR1583999A (en) 1969-12-12
IE32152L (en) 1969-01-05
US3732229A (en) 1973-05-08
NL6809422A (en) 1969-01-07
IL30313A0 (en) 1968-09-26
IL30313A (en) 1972-08-30
SE352891B (en) 1973-01-15
CH496005A (en) 1970-09-15

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