ES355739A1 - 3-cyclohexyl phenyl-2-hydroxypropyl-4-phenyl piperazines - Google Patents

3-cyclohexyl phenyl-2-hydroxypropyl-4-phenyl piperazines

Info

Publication number
ES355739A1
ES355739A1 ES355739A ES355739A ES355739A1 ES 355739 A1 ES355739 A1 ES 355739A1 ES 355739 A ES355739 A ES 355739A ES 355739 A ES355739 A ES 355739A ES 355739 A1 ES355739 A1 ES 355739A1
Authority
ES
Spain
Prior art keywords
prepared
chloro
phenyl
carbon atoms
piperazine
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
ES355739A
Other languages
Spanish (es)
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
Publication of ES355739A1 publication Critical patent/ES355739A1/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

Novel piperazine derivatives having the general formula where R = hydrogen or alkoxy (containing from 1-8 carbon atoms in a straight or branched chain). R1 = 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. R2 = hydrogen or methyl R3 = 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, R1 and R2 have the same meanings as above, and a base with a substituted piperazine having the formula where R3 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.
ES355739A 1967-07-05 1968-07-04 3-cyclohexyl phenyl-2-hydroxypropyl-4-phenyl piperazines Expired ES355739A1 (en)

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
ES355739A1 true ES355739A1 (en) 1969-12-16

Family

ID=10314465

Family Applications (1)

Application Number Title Priority Date Filing Date
ES355739A Expired ES355739A1 (en) 1967-07-05 1968-07-04 3-cyclohexyl phenyl-2-hydroxypropyl-4-phenyl piperazines

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)

Families Citing this family (6)

* 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
GB9308725D0 (en) * 1993-04-27 1993-06-09 Wyeth John & Brother Ltd Piperazine derivatives
AU2868601A (en) * 2000-01-27 2001-08-07 Ribotargets Ltd Biaryl compounds, their preparation and their use in therapy
JO2857B1 (en) * 2008-06-16 2015-03-15 سانوفي أفينتس Phenyl-alkylpiperazines with tnf-modulating activity

Also Published As

Publication number Publication date
IL30313A0 (en) 1968-09-26
GB1171251A (en) 1969-11-19
IE32152B1 (en) 1973-05-02
NO126082B (en) 1972-12-18
DK120998B (en) 1971-08-16
SE352891B (en) 1973-01-15
FR1583999A (en) 1969-12-12
IE32152L (en) 1969-01-05
AT281038B (en) 1970-05-11
US3732229A (en) 1973-05-08
DE1770805A1 (en) 1972-01-13
NL6809422A (en) 1969-01-07
CH496005A (en) 1970-09-15
IL30313A (en) 1972-08-30

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