GB448181A - Manufacture of basic esters of polyarylacetic acids - Google Patents

Manufacture of basic esters of polyarylacetic acids

Info

Publication number
GB448181A
GB448181A GB33727/34A GB3372734A GB448181A GB 448181 A GB448181 A GB 448181A GB 33727/34 A GB33727/34 A GB 33727/34A GB 3372734 A GB3372734 A GB 3372734A GB 448181 A GB448181 A GB 448181A
Authority
GB
United Kingdom
Prior art keywords
ester
acid
ethylene
diphenylacetic acid
polyarylacetic
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
GB33727/34A
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.)
BASF Schweiz AG
Original Assignee
Gesellschaft fuer Chemische Industrie in Basel CIBA
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 Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Publication of GB448181A publication Critical patent/GB448181A/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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups

Landscapes

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

Abstract

Basic esters are made by reacting (1) an amino-alkanol disubstituted in the amino group with a polyarylacetic acid or a halide, ester or anhydride thereof in presence or absence of a condensing agent; (2) a reactive ester of such an amino-alkanol with a polyarylacetic acid or a salt thereof; (3) an alkylene halogenhydrin with a polyarylacetic acid or a halide, ester or anhydride thereof and treating the product with a secondary amine; or (4) an alkylene halogenhydrin or an alkylene dihalide with a salt of a polyarylacetic acid, replacing by halogen any hydroxyl group which may be present by treating with a halogenating agent, and then reacting with a secondary amine. Quaternary ammonium compounds of the basic esters so produced may be made by the addition of an alkyl halide, an alkylene halide, an aryl sulphonic acid ester, a dialkyl sulphate, or an arylalkyl halide. Reactive esters of aminoalkanols specified are those with hydrohalogen acids or arylsulphonic acids. The new compounds are used therapeutically. In examples: (1) diphenylacetyl chloride or diphenyl-acetic acid methyl or ethyl ester is reacted with diethylaminoethanol; (2) diphenylacetic acid with chlorethyldiethylamine hydrochloride; (3) diphenylacetyl chloride with allyl-ethyl-aminoethanol; (4) triphenyl-acetyl chloride with diethylamino - ethanol; (5) diphenylacetyl chloride with ethylene chlorhydrin, and the diphenylacetic acid-2-chlorethanol ester so obtained with diethylamine, or alternatively the chlor-ethanol ester is made by reacting an alkali salt of diphenylacetic acid with an ethylene dihalide or an ethylene halogen-hydrin, in the latter case treating the oxyethanol ester obtained with thionyl chloride. Ethylene bromhydrin may replace ethylene chlorhydrin, and ethylene dihalides specified are ethylene chlorobromide, ethylene bromide or ethylene iodide. Other products of the invention are diphenylacetic acid - 2 - methyl - ethylaminoethanol ester, diphenylacetic acid-2-di-n-butylamino-ethanol ester, diphenylacetic acid-2-piperidinoethanol ester, diphenylacetic acid-1-methyl - 3 - diethylaminopropanol ester, and diphenylacetic acid - m - dimethyl - aminocyclohexanol ester. Methylethylaminoethanol is made from ethylaminoethanol and formaldehyde in presence of formic acid. 1-Methyl-3-diethylaminopropanol is made by reduction of diethylamino-methyl ketone in ethereal solution by means of activated aluminium. m - Dimethylamino - cyclohexanol is made by methylating m-amino-cyclohexanol, itself obtained from m-acetylaminophenol by catalytic reduction followed by saponification. Allyl - ethylaminoethanol is prepared from allyl bromide and ethylamino-ethanol. 2 - Di - n - butylaminoethanol is made from ethylene chlorhydrin and di-n-butylamine. Diphenylacetyl chloride is made by the action of thionyl chloride on diphenylacetic acid.
GB33727/34A 1934-07-12 1934-11-23 Manufacture of basic esters of polyarylacetic acids Expired GB448181A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH2079962X 1934-07-12

Publications (1)

Publication Number Publication Date
GB448181A true GB448181A (en) 1936-05-25

Family

ID=31994866

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33727/34A Expired GB448181A (en) 1934-07-12 1934-11-23 Manufacture of basic esters of polyarylacetic acids

Country Status (5)

Country Link
US (1) US2079962A (en)
DE (3) DE626539C (en)
FR (1) FR795597A (en)
GB (1) GB448181A (en)
NL (1) NL42150C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US3014913A (en) * 1959-11-16 1961-12-26 Upjohn Co Ortho-alkanoyloxy-benzoates of n-phenylethyl-4-piperidinol

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2648666A (en) * 1953-08-11 Quaternary ammonium salts derived
DE763489C (en) * 1937-11-09 1951-08-09 Friedrich Dr Luther Process for the preparation of ª-aminoethyl esters of substituted phenylacetic acids
US2447395A (en) * 1940-07-05 1948-08-17 Parke Davis & Co Morpholine substituted esters
US2446522A (en) * 1940-07-08 1948-08-10 Winthrop Stearns Inc Diaryl nitrogenous heterocyclic alkylene compounds
US2423025A (en) * 1942-03-31 1947-06-24 American Cyanamid Co Alkamine esters of diarylpropionic acids
US2475852A (en) * 1942-04-08 1949-07-12 American Cyanamid Co Morpholinoalkanol esters
US2419366A (en) * 1942-04-08 1947-04-22 American Cyanamid Co Alkanol esters
US2421729A (en) * 1943-05-20 1947-06-03 Burroughs Wellcome Co Production of 3-aryl-1, 5-dibrompentane-3-carboxylic acid
US2474651A (en) * 1944-02-26 1949-06-28 Univ Michigan Basic-alkyl esters and their salts
US2415079A (en) * 1944-02-26 1947-02-04 Regents Basic-alkyl esters and their salts
US2489950A (en) * 1944-02-26 1949-11-29 Univ Michigan Basic-alkyl esters and their salts
US2533084A (en) * 1946-08-17 1950-12-05 Univ Michigan Aminoalkyl esters of dithienyl aliphatic acids
US2607777A (en) * 1947-04-10 1952-08-19 Searle & Co N-alkyl piperidyl alkyl esters of diphenyl acetic acid and 9-fluorenyl carboxylic acid
US2589937A (en) * 1947-05-23 1952-03-18 Geigy Ag J R Manufacture of new basic esters of 1-aryl-cyclopentane-1-monothiocarboxylic acids
US2662891A (en) * 1948-01-12 1953-12-15 Schering Corp P-chlorophenyl(2-pyridyl) (beta-dimethylaminoethoxy) methane
US2576230A (en) * 1948-02-20 1951-11-27 Searle & Co Aminoalkyl esters of alpha, beta, beta-triarylpropionic acids
US2512307A (en) * 1948-07-24 1950-06-20 Sterling Drug Inc Esters of di-substituted acetic acids and sulfur containing tertiary amino alkanols
US2659725A (en) * 1950-06-21 1953-11-17 Searle & Co Quaternary ammonium salts of heterocyclylalkanol esters of xanthene-9-carboxylic acid
US2918407A (en) * 1957-04-08 1959-12-22 Lakeside Lab Inc Anti-spasmodics specific for upper gastrointestinal pain and spasm
DE1162846B (en) * 1961-08-17 1964-02-13 C. F. Boehringer & Soehne G.m. b.H., Mannheim-Waldhof Process for the preparation of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes and their salts.
DE1162845B (en) * 1961-08-16 1964-02-13 C. F. Boehringer &. Soehne G.m. b.H., Mannheim-Waldhof Process for the preparation of the hydrohalides of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes.
DE1163844B (en) * 1960-11-26 1964-02-27 C F Boehrm^er S. Soehne G m bH Mannheim Wildhof Process for the preparation of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes and their hydrohalides.
US3174994A (en) * 1962-01-30 1965-03-23 Smith Kline French Lab Hypocholesterolemic n-oxide compositions
DE3544172A1 (en) * 1985-12-13 1987-06-19 Lentia Gmbh NEW CRYSTALLINE SALTS OF ARYLOXY PROPANOLAMINES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE
US4973734A (en) * 1989-03-17 1990-11-27 The United States Of America As Represented By The Secretary Of The Army Carbaphens: aprophen analogs that are binary antidotes for organophosphate poisoning

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US3014913A (en) * 1959-11-16 1961-12-26 Upjohn Co Ortho-alkanoyloxy-benzoates of n-phenylethyl-4-piperidinol

Also Published As

Publication number Publication date
DE680662C (en) 1939-09-06
DE626539C (en) 1936-02-27
NL42150C (en) 1937-12-15
FR795597A (en) 1936-03-17
DE653778C (en) 1937-12-02
US2079962A (en) 1937-05-11

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