GB448181A - Manufacture of basic esters of polyarylacetic acids - Google Patents
Manufacture of basic esters of polyarylacetic acidsInfo
- 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
Links
- 150000002148 esters Chemical class 0.000 title abstract 8
- 239000002253 acid Substances 0.000 title abstract 7
- 150000007513 acids Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 alkylene halide Chemical class 0.000 abstract 10
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 abstract 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 4
- 239000005977 Ethylene Substances 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract 3
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 abstract 3
- XGIKILRODBEJIL-UHFFFAOYSA-N 1-(ethylamino)ethanol Chemical compound CCNC(C)O XGIKILRODBEJIL-UHFFFAOYSA-N 0.000 abstract 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 150000003335 secondary amines Chemical class 0.000 abstract 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 abstract 1
- GBBZLMLLFVFKJM-UHFFFAOYSA-N 1,2-diiodoethane Chemical compound ICCI GBBZLMLLFVFKJM-UHFFFAOYSA-N 0.000 abstract 1
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 abstract 1
- UOZBNMMELVBICG-UHFFFAOYSA-N 2,2,2-triphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)Cl)C1=CC=CC=C1 UOZBNMMELVBICG-UHFFFAOYSA-N 0.000 abstract 1
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 abstract 1
- HZLYGAQNCRJBDT-UHFFFAOYSA-N 2-(ethylamino)propan-2-ol Chemical compound CCNC(C)(C)O HZLYGAQNCRJBDT-UHFFFAOYSA-N 0.000 abstract 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- PYYBPWSWSPMKTL-UHFFFAOYSA-N 3-(dimethylamino)cyclohexan-1-ol Chemical compound CN(C)C1CCCC(O)C1 PYYBPWSWSPMKTL-UHFFFAOYSA-N 0.000 abstract 1
- NIQIPYGXPZUDDP-UHFFFAOYSA-N 3-aminocyclohexan-1-ol Chemical compound NC1CCCC(O)C1 NIQIPYGXPZUDDP-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- QUDBKQDNUJKSAM-UHFFFAOYSA-N 4-(diethylamino)butan-2-ol Chemical compound CCN(CC)CCC(C)O QUDBKQDNUJKSAM-UHFFFAOYSA-N 0.000 abstract 1
- WLIDMSAGUGOWHZ-UHFFFAOYSA-N C(C)N(CC)CC(=O)CN(CC)CC Chemical compound C(C)N(CC)CC(=O)CN(CC)CC WLIDMSAGUGOWHZ-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 150000001447 alkali salts Chemical class 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001398 aluminium Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 abstract 1
- AORIUCNKPVHMTN-UHFFFAOYSA-N methyl 2,2-diphenylacetate Chemical group C=1C=CC=CC=1C(C(=O)OC)C1=CC=CC=C1 AORIUCNKPVHMTN-UHFFFAOYSA-N 0.000 abstract 1
- 230000001035 methylating effect Effects 0.000 abstract 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
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)
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 (enrdf_load_stackoverflow) |
| DE (3) | DE626539C (enrdf_load_stackoverflow) |
| FR (1) | FR795597A (enrdf_load_stackoverflow) |
| GB (1) | GB448181A (enrdf_load_stackoverflow) |
| NL (1) | NL42150C (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2995560A (en) * | 1959-09-11 | 1961-08-08 | Lakeside Lab Inc | Acetates of 3-piperidinol |
| US2995492A (en) * | 1957-12-23 | 1961-08-08 | Lakeside Lab Inc | Piperidine derivatives with psychotogenic activity |
| US3014913A (en) * | 1959-11-16 | 1961-12-26 | Upjohn Co | Ortho-alkanoyloxy-benzoates of n-phenylethyl-4-piperidinol |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2648666A (en) * | 1953-08-11 | Quaternary ammonium salts derived | ||
| DE763489C (de) * | 1937-11-09 | 1951-08-09 | Friedrich Dr Luther | Verfahren zur Herstellung von ª-Aminoaethylestern substituierter Phenylessigsaeuren |
| 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 |
| US2419366A (en) * | 1942-04-08 | 1947-04-22 | American Cyanamid Co | Alkanol esters |
| US2475852A (en) * | 1942-04-08 | 1949-07-12 | American Cyanamid Co | Morpholinoalkanol 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 (de) * | 1961-08-17 | 1964-02-13 | C. F. Boehringer & Soehne G.m. b.H., Mannheim-Waldhof | Verfahren zur Herstellung von Estern von N-(Hydroxyalkyl)-nortropanen bzw.-norgranatanen und ihren Salzen. |
| DE1163844B (de) * | 1960-11-26 | 1964-02-27 | C F Boehrm^er S. Soehne G m bH Mannheim Wildhof | Verfahren zur Herstellung von Estern von N-(Hydroxyalkyl)-nortropanen bzw. -norgranatanen und ihren Hydrohalogeniden. |
| DE1162845B (de) * | 1961-08-16 | 1964-02-13 | C. F. Boehringer &. Soehne G.m. b.H., Mannheim-Waldhof | Verfahren zur Herstellung der Hydrohalogenide von Estern von N-(Hydroxyalkyl)-nortropanen bzw.-norgranatanen. |
| US3174994A (en) * | 1962-01-30 | 1965-03-23 | Smith Kline French Lab | Hypocholesterolemic n-oxide compositions |
| DE3544172A1 (de) * | 1985-12-13 | 1987-06-19 | Lentia Gmbh | Neue kristalline salze von aryloxy-propanolaminen, verfahren zu ihrer herstellung und ihre verwendung |
| 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 |
-
1934
- 1934-11-23 GB GB33727/34A patent/GB448181A/en not_active Expired
- 1934-11-24 DE DEG89225D patent/DE626539C/de not_active Expired
-
1935
- 1935-06-26 NL NL74027A patent/NL42150C/xx active
- 1935-07-06 US US30166A patent/US2079962A/en not_active Expired - Lifetime
- 1935-07-10 FR FR795597D patent/FR795597A/fr not_active Expired
-
1936
- 1936-04-12 DE DEG92670D patent/DE653778C/de not_active Expired
-
1937
- 1937-04-22 DE DEG95279D patent/DE680662C/de not_active Expired
Cited By (3)
| 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 |
|---|---|
| DE626539C (de) | 1936-02-27 |
| DE653778C (de) | 1937-12-02 |
| US2079962A (en) | 1937-05-11 |
| FR795597A (fr) | 1936-03-17 |
| DE680662C (de) | 1939-09-06 |
| NL42150C (enrdf_load_stackoverflow) | 1937-12-15 |
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