GB807750A - Improvements in or relating to piperazine derivatives - Google Patents

Improvements in or relating to piperazine derivatives

Info

Publication number
GB807750A
GB807750A GB18086/57A GB1808657A GB807750A GB 807750 A GB807750 A GB 807750A GB 18086/57 A GB18086/57 A GB 18086/57A GB 1808657 A GB1808657 A GB 1808657A GB 807750 A GB807750 A GB 807750A
Authority
GB
United Kingdom
Prior art keywords
piperazine
give
heated
hydroxypropyl
sodium hydroxide
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
GB18086/57A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Societe des Usines Chimiques Rhone Poulenc SA
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 Rhone Poulenc SA, Societe des Usines Chimiques Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB807750A publication Critical patent/GB807750A/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
    • C07D295/08—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
    • C07D295/088—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 to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises new piperazine derivatives of formula <FORM:0807750/IV (b)/1> in which R represents an hydrogen atom or an alkyl, aryl, hydroxyalkyl, tetrahydropyranyloxyalkyl, o -(dialkoxy)-alkyl, hydroxyalkoxyalkyl or tetrahydropyranyl oxyalkoxyalkyl group and R1 represents an hydrogen atom or a methyl group. They are prepared by reacting allyl or methallyl alcohol with a piperazine of general formula <FORM:0807750/IV (b)/2> by heating the reactants with or without a solvent using substantially anhydrous condtions in the presence of a strong base, e.g. an alkali metal hydroxide or alcoholate, preferably sodium allylate. As a solvent there may be used an alcohol or other solvent stable in a basic medium. In the examples: (a) allyl alcohol, 1-methylpiperazine and sodium hydroxide are heated under reflux and 1-methyl-4-(3-hydroxypropyl)-piperazine is separated from the resulting mixture; (b) allyl alcohol, anhydrous piperazine and sodium hydroxide are heated to give 1-(3-hydroxypropyl)-piperazine; (c) allyl alcohol, piperazine, isoamyl alcohol and sodium hydroxide are heated to give 1-(3-hydroxypropyl)-piperazine; (d) allyl alcohol, piperazine and potassium hydroxide are heated to give 1-(3-hydroxypropyl)-piperazine; (e) 1-methylpiperazine is added to a solution of sodium in allyl alcohol and the mixture is heated to give 1 - methyl - 4 - (3 - hydroxypropyl) - piperazine; (f) 1-phenyl piperazine, allyl alcohol and sodium hydroxide are heated to give 1-phenyl-4-(3-hydroxypropyl)-piperazine; (g) 1-(2-hydroxyethyl)-piperazine, allyl alcohol and sodium hydroxide are heated to give 1-(2-hydroxyethyl)-4-(3-hydroxypropyl)-piperazine; (g) 1-(2-hydroxyethyl)-piperazine, allyl alcohol and sodium hydroxide are heated to give 1-(2-hydroxyethyl) - 4 - (3 - hydroxypropyl) - piperazine; (h) 1-(2-tetrapyranyloxyethyl)-piperazine, sodium hydroxide and allyl alcohol to give 1 - (2 - tetrahydropyranyloxyethyl) - 4 - (3 - hydroxypropyl) - piperazine; (j) 1 - (2,2 - diethoxyethyl) - piperazine, allyl alcohol and sodium hydroxide are heated to give 1-(2,2-diethoxyethyl) - 4 - (3 - hydroxypropyl) - piperazine; (k) 1-(2-hydroxyethoxyethyl)-piperazine, allyl alcohol and sodium hydroxide are heated to give 1-(2-hydroxyethoxyethyl)-4-(3-hydroxypropyl)-piperazine; (l) 1-(2-tetrahydropyranyloxyethoxyethyl)-piperazine, allyl alcohol and sodium hydroxide are heated to give 1-(2-tetrahydropyranyloxyethoxyethyl) - 4 - (3 - hydroxypropyl) - piperazine; (m) 1 - methylpiperazine, methallyl alcohol and sodium hydroxide are heated to give 1-methyl-4-(3-hydroxy-2-methyl-1-propyl)-piperazine; and (n) piperazine, methallyl alcohol and sodium hydroxide are heated to give 1-(3-hydroxy-2-methyl-1-propyl)-piperazine.
GB18086/57A 1956-06-15 1957-06-06 Improvements in or relating to piperazine derivatives Expired GB807750A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR807750X 1956-06-15

Publications (1)

Publication Number Publication Date
GB807750A true GB807750A (en) 1959-01-21

Family

ID=9252594

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18086/57A Expired GB807750A (en) 1956-06-15 1957-06-06 Improvements in or relating to piperazine derivatives

Country Status (1)

Country Link
GB (1) GB807750A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4590223A (en) * 1982-03-23 1986-05-20 Toyo Soda Manufacturing Co., Ltd. Producing polyurethanes using hydroxy-alkyl piperazine catalyst compositions
WO2007014941A2 (en) * 2005-08-03 2007-02-08 Janssen Pharmaceutica N.V. Quinoline derivatives as antibacterial agents

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4590223A (en) * 1982-03-23 1986-05-20 Toyo Soda Manufacturing Co., Ltd. Producing polyurethanes using hydroxy-alkyl piperazine catalyst compositions
WO2007014941A2 (en) * 2005-08-03 2007-02-08 Janssen Pharmaceutica N.V. Quinoline derivatives as antibacterial agents
WO2007014941A3 (en) * 2005-08-03 2007-03-29 Janssen Pharmaceutica Nv Quinoline derivatives as antibacterial agents
EA014833B1 (en) * 2005-08-03 2011-02-28 Янссен Фармацевтика Н.В. Quinoline derivatives as antibacterial agents
AP2654A (en) * 2005-08-03 2013-04-25 Janssen Pharmaceutica Nv Quinoline derivatives as antibacterial agents
US8802671B2 (en) 2005-08-03 2014-08-12 Janssen Pharmaceutica Nv Quinoline derivatives as antibacterial agents
NO341242B1 (en) * 2005-08-03 2017-09-25 Janssen Pharmaceutica Nv Quinoline derivatives as antibacterial agents

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