GB770581A - Heterocyclic alcohol diammonio esters - Google Patents

Heterocyclic alcohol diammonio esters

Info

Publication number
GB770581A
GB770581A GB8626/55A GB862655A GB770581A GB 770581 A GB770581 A GB 770581A GB 8626/55 A GB8626/55 A GB 8626/55A GB 862655 A GB862655 A GB 862655A GB 770581 A GB770581 A GB 770581A
Authority
GB
United Kingdom
Prior art keywords
iodide
reacting
ethyl
anion
methyl
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
GB8626/55A
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.)
Bayer Corp
Original Assignee
Cutter Laboratories Inc
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 Cutter Laboratories Inc filed Critical Cutter Laboratories Inc
Publication of GB770581A publication Critical patent/GB770581A/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
    • 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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero 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 compounds of the formula <FORM:0770581/IV(b)/1> wherein n and m are integers from 1 to 6 inclusive, R, R1, R11 and R111 are alkyl groups containing up to 6 carbon atoms and the group -N\s6A represents a heterocyclic radical such as piperidyl, pyrrolidyl, morpholinyl or alkylpiperidyl and wherein the anion is a non-toxic anion. Such compounds are obtained by reacting a compound of the general formula <FORM:0770581/IV(b)/2> where X represents Cl, Br or I with a trialkyl amine NRR1R11. Products in the above formula where R11 and R111 are alike can also be prepared by reacting a compound of the formula <FORM:0770581/IV(b)/3> with a quaternizing agent of the formula R11-anion or R111-anion. "Anion" may represent for example chloride, bromide, iodide, nitrate, tartrate, sulphate, citrate or picrate. One ion may be replaced by another by transhalogenation or using ion-exchange methods. In Example (1), 2-(1-ethylpiperidinio)ethanol iodide and 3-iodopropionyl iodide are reacted and the product is quaternated with trimethylamine to give 2-(1-ethylpiperidinio)ethyl 3-trimethylammoniopropionate diiodide. Other halides are referred to. In a generally similar manner are prepared (2) 2-(1-methylpiperidinio) ethyl 3-trimethylammoniopropionate diiodide; (3) 2-(1-methylpyrrolidinio)ethyl 3-trimethylammoniopropionate diiodide; (4) 2-(4-methylmorpholinio)ethyl 3-trimethylammoniopropionate diiodide. In further examples, (5) 1-methyl2-(4-methyl-1-piperidyl)ethyl 3-dimethylaminopropionate is quaternated by reaction with methyl iodide. Reference is made to the preparation of compounds containing other radicals within the scope of the above formula, list of radicals being given; (6) to (9), the product of Example (1) is converted to the dichloride dinitrate, dibitartrate, and dipicrate, respectively by (6) passage over an anion-exchange resin in the chloride state; (7) reaction with silver nitrate; (8) reaction with silver bitartrate; (9) reaction with picric acid. Starting materials. 3-Iodopropionyl chloride is prepared by reacting 3-iodopropionic acid with phosphorus trichloride. 2-(1-Ethylpiperidinio)ethanol iodide is obtained by reacting 1-ethylpiperidine and 2-iodoethanol. 2-(1-Methylpiperidinio) ethanol iodide is obtained by reacting 1-piperidineethanol and methyl iodide. a ,4 - Dimethyl - 1 - piperidineethanol is obtained by reacting 4-pipecoline and propylene oxide. Acrylyl chloride and a ,4-dimethylpiperidine-ethanol are reacted to form 1-methyl-2-(4-methyl - 1 - piperidyl) ethyl 3 - dimethylaminopropionate.
GB8626/55A 1954-10-14 1955-03-24 Heterocyclic alcohol diammonio esters Expired GB770581A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US770581XA 1954-10-14 1954-10-14

Publications (1)

Publication Number Publication Date
GB770581A true GB770581A (en) 1957-03-20

Family

ID=22135824

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8626/55A Expired GB770581A (en) 1954-10-14 1955-03-24 Heterocyclic alcohol diammonio esters

Country Status (1)

Country Link
GB (1) GB770581A (en)

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