GB601612A - Process for the preparation of amino-derivatives of dioxa-cyclopentane and quaternary salts derived therefrom - Google Patents

Process for the preparation of amino-derivatives of dioxa-cyclopentane and quaternary salts derived therefrom

Info

Publication number
GB601612A
GB601612A GB15045/45A GB1504545A GB601612A GB 601612 A GB601612 A GB 601612A GB 15045/45 A GB15045/45 A GB 15045/45A GB 1504545 A GB1504545 A GB 1504545A GB 601612 A GB601612 A GB 601612A
Authority
GB
United Kingdom
Prior art keywords
dioxacyclopentane
chlormethyl
alkyl
quaternary salts
dioxacyclopentanes
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
GB15045/45A
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
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 filed Critical Rhone Poulenc SA
Publication of GB601612A publication Critical patent/GB601612A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/28—Radicals substituted by nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Substituted aminomethyl dioxacyclopentanes of the general formula <FORM:0601612/IV(b)/1> (wherein R represents a lower alkyl group, R1 represents hydrogen or alkyl and R2 represents hydrogen, alkyl or aryl) are manufactured by reacting cyclic acetals of glycerol a -halohydrins with dialkylamines, and the corresponding quaternary salts, which have physiological properties similar to those of acetylcholine, are obtained by treating the products with an alkyl halide. In examples: (1) the formal of glycerol a -monochlorhydrin is heated at 160 DEG C. with anhydrous dimethylamine in benzene to produce 4-dimethylaminomethyl-1 : 3-dioxacyclopentane, which is treated with methyliodide to obtain the corresponding methiodide; the process of (1) is applied to (2) 4-chlormethyl-2-methyl - 1 : 3 - dioxacyclopentane; (3) 4 - chlormethyl-2 : 2-dimethyl-1 : 3-dioxacyclopentane, and (4) 4-chlormethyl-1 : 3-dioxacyclopentane, to obtain the corresponding aminomethyl-dioxacyclopentanes and their methiodides. 4-Chlormethyl-2 : 2-dimethyl-1 : 3-dioxacyclopentane is obtained by condensing acetone with epichlorhydrin in presence of tin tetrachloride. 4 - Chlormethyl - 2 - phenyl - 1 : 3 - dioxacyclo - pentane is obtained similarly from benzaldehyde. The Specification as open to inspection under Sect. 91 comprises also the manufacture of products of the general formula above in which R2 represents an aralkyl group. This subject-matter does not appear in the Specification as accepted.
GB15045/45A 1944-03-08 1945-06-13 Process for the preparation of amino-derivatives of dioxa-cyclopentane and quaternary salts derived therefrom Expired GB601612A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR601612X 1944-03-08

Publications (1)

Publication Number Publication Date
GB601612A true GB601612A (en) 1948-05-10

Family

ID=8971380

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15045/45A Expired GB601612A (en) 1944-03-08 1945-06-13 Process for the preparation of amino-derivatives of dioxa-cyclopentane and quaternary salts derived therefrom

Country Status (1)

Country Link
GB (1) GB601612A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0097822A1 (en) * 1982-06-04 1984-01-11 Bayer Ag Aminomethyldioxolanes as parasiticides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0097822A1 (en) * 1982-06-04 1984-01-11 Bayer Ag Aminomethyldioxolanes as parasiticides
US4503059A (en) * 1982-06-04 1985-03-05 Bayer Aktiengesellschaft 1,3-Dioxacyclopentanes, their pesticidal use and compositions for pesticidal use
US4668700A (en) * 1982-06-04 1987-05-26 Bayer Aktiengesellschaft Pest-combating agents

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