GB782935A - Heterocyclic acid diammonio esters - Google Patents

Heterocyclic acid diammonio esters

Info

Publication number
GB782935A
GB782935A GB8851/55A GB885155A GB782935A GB 782935 A GB782935 A GB 782935A GB 8851/55 A GB8851/55 A GB 8851/55A GB 885155 A GB885155 A GB 885155A GB 782935 A GB782935 A GB 782935A
Authority
GB
United Kingdom
Prior art keywords
iodide
methyl
propionate
ethyl
reacted
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
GB8851/55A
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 GB782935A publication Critical patent/GB782935A/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)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0782935/IV (a)/1> wherein R, R1, R11 and R111 are lower alky groups (containing 1 to 6 carbon atoms), n and m are integers from 1 to 6 inclusive and the group <FORM:0782935/IV (a)/2> represents a heterocyclic radical such as pyrrolidyl, morpholinyl, piperidyl and alkylsubstituted-piperidyl and the anions are nontoxic quaternary salt forming anions. Such compounds are obtained by reacting a compound of the formula <FORM:0782935/IV (a)/3> with a quaternizing agent of the formula R11 anion or R111-anion or by reacting a compound of the formula <FORM:0782935/IV (a)/4> wherein X is chlorine, bromine or iodine, with a compound of the formula <FORM:0782935/IV (a)/5> Anions specified are chloride, bromide, iodide, picrate, sulphate, nitrate, citrate and bitartrate, and one may be exchanged for the other by, for example, treating the products with an anionexchange resin. In examples: (1) 2-dimethylaminoethyl a - methyl - 1 - pyrrolidinopropionate is quaternated with methyl iodide, giving 2-trimethylammonioethyl 2-methyl-3-(1 - methylpyrrolidinio) propionate di-iodide. Similarly obtained are (2) 2-trimethylammonioethyl 2 - methyl - 3 - (4 - methylmorpholinio) - propionate di-iodide; (5) 2 - (butyl - ethylmethylammonio) ethyl 3 - (1 - methylpyrrolidinio) propionate di-iodide; (6) 1-methyl-2-trimethylammonioethyl 3 - (1,4 - dimethylpiperidino) propionate di-iodide; (7) 2-trimethylammonioethyl 3 - (4 - methylmorpholinio) butyrate di-iodide; (8) 2-dimethylethylammonio) ethyl 3-(1-methyl-pyrrolidinio) butyrate di-iodide. In further examples: (3) the product of Example (2) is converted to the dipicrate by reaction with picric acid; (4) 2-trimethylammoniobutyl 3 - iodopropionate iodide and 1-ethylpiperidine are reacted to form 2-trimethylammoniobutyl 3 - (1 - ethyl - piperidinio) propionate di-iodide. Starting materials. 2-Dimethylaminoethyl methacrylate and pyrrolidine are reacted in the presence of N-phenyl-2-naphthylamine to give 2 - dimethylaminoethyl a - methyl - 1 - pyrrolidinepropionate. Similarly obtained is 2-dimethylaminoethyl a -methyl-4-morpholinepropionate. Methyl iodide and 2-amino-1-butanol reacted in the presence of sodium hydroxide give 2-trimethylammoniobutanol iodide. Reaction of this compound with 3-iodo-propionyl chloride gives 2 - trimethylammoniobutyl 3 - iodopropionate iodide. Butylethylamine and ethylene chlorohydrin are reacted to give 2-(butylethylamino)-ethanol. Reaction of the latter with acrylyl chloride gives 2-(butylethylamino) ethyl acrylate, which on reaction with pyrrolidine gives 2-(butylethylamino) ethyl 1-pyrrolidine propionate. Acrylyl chloride and 1-dimethylamino-2-propanol react to form 2-diethylamino-1-methylethyl acrylate, which is refluxed with pipecoline to form 2-dimethylamino-1-methylethyl 4-methyl1-piperidine-propionate. Crotonyl chloride and 2-dimethyl-aminoethanol are reacted to form 2-dimethyl-aminoethyl crotonate and this compound in the presence of N-phenyl-2-naphthylamine reacts with morpholine to form 2-dimethylaminoethyl b -methyl-4-morpholinepropionate. Crotonyl chloride and 2-(ethylmethylamino)-ethanol react to form 2-(ethylmethylamino)-ethyl crotonate, reaction of which with pyrrolidine gives 2-(ethylmethylamino) ethyl b -methyl-1-pyrrolidinepropionate.
GB8851/55A 1954-10-14 1955-03-25 Heterocyclic acid diammonio esters Expired GB782935A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US782935XA 1954-10-14 1954-10-14

Publications (1)

Publication Number Publication Date
GB782935A true GB782935A (en) 1957-09-18

Family

ID=22143109

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8851/55A Expired GB782935A (en) 1954-10-14 1955-03-25 Heterocyclic acid diammonio esters

Country Status (1)

Country Link
GB (1) GB782935A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3828169A4 (en) * 2018-07-24 2022-04-20 West China Hospital, Sichuan University Dication compound, preparation method therefor and use thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3828169A4 (en) * 2018-07-24 2022-04-20 West China Hospital, Sichuan University Dication compound, preparation method therefor and use thereof

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