GB483258A - Manufacture of basic esters of polyarylacetic acids - Google Patents

Manufacture of basic esters of polyarylacetic acids

Info

Publication number
GB483258A
GB483258A GB14860/37A GB1486037A GB483258A GB 483258 A GB483258 A GB 483258A GB 14860/37 A GB14860/37 A GB 14860/37A GB 1486037 A GB1486037 A GB 1486037A GB 483258 A GB483258 A GB 483258A
Authority
GB
United Kingdom
Prior art keywords
acid
tropine
ester
polyarylacetic
pseudo
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
GB14860/37A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of GB483258A publication Critical patent/GB483258A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
    • C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine

Abstract

Basic esters are made by (a) reacting a polyarylacetic acid or a halide, ester, or anhydride thereof with a saturated heterocyclic base containing as ring substituents a hydroxy group and a substituent attached to a ring nitrogen atom, in presence or absence of a condensing agent, or by (b) reacting a reactive ester of such a base with a salt of a polyarylacetic acid, or with the acid itself in presence of an acid-binding agent or by (c) reacting such a base with a diarylketene in presence or absence of a condensing agent. Bases of the type specified are tropine, pseudo-tropine, N-substituted-g -hydroxypiperidines and N-substituted-b -oxypyrolidines. In examples, (1) tropine or pseudo-tropine is reacted with diphenylacetyl chloride or bromide, diphenyl-acetic acid methyl ester, diphenylacetic acid in presence of hydrochloric acid, or with diphenyl ketene in an organic solvent to give the tropine or pseudo-tropine ester of diphenylacetic acid; (2) diphenylacetyl chloride is reacted in chlorbenzene with 1-b -phenyl-ethyl-2.6-dimethyl-4-hydroxypiperidine to give the diphenylacetic ester; the corresponding triphenylacetic acid esters may be obtained similarly. Specification 451,925 is referred to.
GB14860/37A 1936-06-08 1937-05-28 Manufacture of basic esters of polyarylacetic acids Expired GB483258A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH483258X 1936-06-08

Publications (1)

Publication Number Publication Date
GB483258A true GB483258A (en) 1938-04-14

Family

ID=4516372

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14860/37A Expired GB483258A (en) 1936-06-08 1937-05-28 Manufacture of basic esters of polyarylacetic acids

Country Status (1)

Country Link
GB (1) GB483258A (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2506605A (en) * 1943-08-09 1950-05-09 Geigy Ag J R 1-alkyl-4-hydroxy-piperidine esters of alkyl substituted acetic acids
US2507449A (en) * 1944-08-24 1950-05-09 Geigy Ag J R 1-alkyl-4-hydroxypiperidine esters
US2816895A (en) * 1954-11-30 1957-12-17 Hoechst Ag Basic benzilic esters and a process of preparing them
US2956062A (en) * 1959-02-26 1960-10-11 Robins Co Inc A H Esters of amino alcohols
US2995492A (en) * 1957-12-23 1961-08-08 Lakeside Lab Inc Piperidine derivatives with psychotogenic activity
US2995560A (en) * 1959-09-11 1961-08-08 Lakeside Lab Inc Acetates of 3-piperidinol
US3006925A (en) * 1961-10-31 J-pyrrolidyl ethanols
US3014913A (en) * 1959-11-16 1961-12-26 Upjohn Co Ortho-alkanoyloxy-benzoates of n-phenylethyl-4-piperidinol
US3051726A (en) * 1959-09-15 1962-08-28 Lakeside Lab Inc Glycolic acid esters of n-substituted-2-pyrrolidylcarbinols
US3117976A (en) * 1958-11-12 1964-01-14 Beecham Res Lab Nu-alkyl-pyrrolidine-2-methanol, alpha cyclohexyl mandelates
US3157671A (en) * 1964-11-17 Ljl-diethyl-a-hydroxypyrrolidimum
US3185702A (en) * 1959-03-16 1965-05-25 Lunsford Carl Dalton Basic esters of 3-aryl-3-pyrrolidinols
US3252994A (en) * 1959-02-12 1966-05-24 Mead Johnson & Co 1, 2-dimethyl-3-benzyl-3-propionoxy-pyrrolidine
US3256297A (en) * 1958-04-02 1966-06-14 Parke Davis & Co 1, 2-dimethyl and 1, 2, 2 trimethyl-3-phenyl-3-propionyloxy pyrrolidines
US3301869A (en) * 1960-05-16 1967-01-31 Robins Co Inc A H Methobromide and hydrochloride of 1-ethyl-3-pyrrolidyl benzilate

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3157671A (en) * 1964-11-17 Ljl-diethyl-a-hydroxypyrrolidimum
US3006925A (en) * 1961-10-31 J-pyrrolidyl ethanols
US2506605A (en) * 1943-08-09 1950-05-09 Geigy Ag J R 1-alkyl-4-hydroxy-piperidine esters of alkyl substituted acetic acids
US2507449A (en) * 1944-08-24 1950-05-09 Geigy Ag J R 1-alkyl-4-hydroxypiperidine esters
US2816895A (en) * 1954-11-30 1957-12-17 Hoechst Ag Basic benzilic esters and a process of preparing them
US2995492A (en) * 1957-12-23 1961-08-08 Lakeside Lab Inc Piperidine derivatives with psychotogenic activity
US3256297A (en) * 1958-04-02 1966-06-14 Parke Davis & Co 1, 2-dimethyl and 1, 2, 2 trimethyl-3-phenyl-3-propionyloxy pyrrolidines
US3117976A (en) * 1958-11-12 1964-01-14 Beecham Res Lab Nu-alkyl-pyrrolidine-2-methanol, alpha cyclohexyl mandelates
US3252994A (en) * 1959-02-12 1966-05-24 Mead Johnson & Co 1, 2-dimethyl-3-benzyl-3-propionoxy-pyrrolidine
US2956062A (en) * 1959-02-26 1960-10-11 Robins Co Inc A H Esters of amino alcohols
US3185702A (en) * 1959-03-16 1965-05-25 Lunsford Carl Dalton Basic esters of 3-aryl-3-pyrrolidinols
US2995560A (en) * 1959-09-11 1961-08-08 Lakeside Lab Inc Acetates of 3-piperidinol
US3051726A (en) * 1959-09-15 1962-08-28 Lakeside Lab Inc Glycolic acid esters of n-substituted-2-pyrrolidylcarbinols
US3014913A (en) * 1959-11-16 1961-12-26 Upjohn Co Ortho-alkanoyloxy-benzoates of n-phenylethyl-4-piperidinol
US3301869A (en) * 1960-05-16 1967-01-31 Robins Co Inc A H Methobromide and hydrochloride of 1-ethyl-3-pyrrolidyl benzilate

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