NO123221B - - Google Patents
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- Publication number
- NO123221B NO123221B NO166201*1A NO16620166A NO123221B NO 123221 B NO123221 B NO 123221B NO 16620166 A NO16620166 A NO 16620166A NO 123221 B NO123221 B NO 123221B
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- denotes
- piperidine
- carboxylic acid
- compound
- Prior art date
Links
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- -1 malonic acid aryl amide ester Chemical class 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 235000013312 flour Nutrition 0.000 claims 1
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000009935 nitrosation Effects 0.000 description 3
- 238000007034 nitrosation reaction Methods 0.000 description 3
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004157 Nitrosyl chloride Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- BMQVDVJKPMGHDO-UHFFFAOYSA-K magnesium;potassium;chloride;sulfate;trihydrate Chemical compound O.O.O.[Mg+2].[Cl-].[K+].[O-]S([O-])(=O)=O BMQVDVJKPMGHDO-UHFFFAOYSA-K 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH10066A CH475986A (de) | 1965-12-30 | 1965-12-30 | Verfahren zur Herstellung von neuen Tetrahydrochinolinderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123221B true NO123221B (pt) | 1971-10-18 |
Family
ID=4179246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO166201*1A NO123221B (pt) | 1965-12-30 | 1966-12-29 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3511842A (pt) |
| AT (3) | AT266136B (pt) |
| CH (1) | CH475986A (pt) |
| CS (1) | CS152273B2 (pt) |
| ES (3) | ES335083A1 (pt) |
| FI (1) | FI48587C (pt) |
| FR (2) | FR1510258A (pt) |
| GB (1) | GB1120700A (pt) |
| IL (1) | IL27187A (pt) |
| NL (1) | NL6618360A (pt) |
| NO (1) | NO123221B (pt) |
| SE (1) | SE305218B (pt) |
| YU (3) | YU32697B (pt) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR066162A1 (es) | 2007-07-31 | 2009-07-29 | Bayer Cropscience Sa | Derivados fungicidas de n- cicloalquil -n- carboxamida- biciclica |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3178434A (en) * | 1965-04-13 | Substituted x-amino-carbostyrils | ||
| US2333493A (en) * | 1941-06-11 | 1943-11-02 | Certificate op correction | |
| US2554737A (en) * | 1949-07-22 | 1951-05-29 | Geigy Ag J R | Basically substituted tetrahydroquinoline derivatives |
| US2653940A (en) * | 1951-01-27 | 1953-09-29 | William S Johnson | Process for preparing 4-quinolyl secondary amines |
| US2786845A (en) * | 1953-05-23 | 1957-03-26 | Elfriede Mauss | Isomeric mixtures of 6-methyl-5-chloro-and 7-chloro-1, 2, 3, 4-tetrahydroquino-line derivatives |
| US2794020A (en) * | 1953-08-03 | 1957-05-28 | Monsanto Chemicals | 6-amino substituted 1, 2, 3, 4-tetrahydroquinolines |
| CH414637A (de) * | 1962-08-31 | 1966-06-15 | Geigy Ag J R | Verfahren zur Herstellung von Carbostyrilderivaten |
| US3332954A (en) * | 1963-02-25 | 1967-07-25 | Evald L Skau | N-oleoyl-1, 2, 3, 4-tetrahydroquinoline |
| US3452026A (en) * | 1966-03-15 | 1969-06-24 | Bristol Myers Co | Substituted 1,2,3,4-tetrahydroquinolines |
| US3384640A (en) * | 1966-03-15 | 1968-05-21 | Bristol Myers Co | Amino isoquinolinium salts |
-
1965
- 1965-12-30 CH CH10066A patent/CH475986A/de not_active IP Right Cessation
-
1966
- 1966-12-20 ES ES335083A patent/ES335083A1/es not_active Expired
- 1966-12-27 US US604624A patent/US3511842A/en not_active Expired - Lifetime
- 1966-12-27 YU YU2447/66A patent/YU32697B/xx unknown
- 1966-12-29 FI FI663479A patent/FI48587C/fi active
- 1966-12-29 CS CS8375A patent/CS152273B2/cs unknown
- 1966-12-29 GB GB58113/66A patent/GB1120700A/en not_active Expired
- 1966-12-29 IL IL27187A patent/IL27187A/en unknown
- 1966-12-29 NO NO166201*1A patent/NO123221B/no unknown
- 1966-12-29 ES ES335082A patent/ES335082A1/es not_active Expired
- 1966-12-29 AT AT1198166A patent/AT266136B/de active
- 1966-12-29 ES ES335081A patent/ES335081A1/es not_active Expired
- 1966-12-29 SE SE17867/66A patent/SE305218B/xx unknown
- 1966-12-29 NL NL6618360A patent/NL6618360A/xx unknown
- 1966-12-29 AT AT1056067A patent/AT266138B/de active
- 1966-12-29 AT AT1055967A patent/AT267528B/de active
- 1966-12-30 FR FR89567A patent/FR1510258A/fr not_active Expired
-
1967
- 1967-03-28 FR FR100459A patent/FR6298M/fr not_active Expired
-
1972
- 1972-06-09 YU YU1555/72A patent/YU33070B/xx unknown
- 1972-06-09 YU YU1554/72A patent/YU33192B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU33192B (en) | 1976-06-30 |
| AT266138B (de) | 1968-11-11 |
| ES335082A1 (es) | 1968-03-01 |
| ES335083A1 (es) | 1968-03-01 |
| ES335081A1 (es) | 1968-03-01 |
| IL27187A (en) | 1970-11-30 |
| YU244766A (en) | 1974-12-31 |
| FR6298M (pt) | 1968-09-09 |
| YU155472A (en) | 1975-12-31 |
| FR1510258A (fr) | 1968-01-19 |
| CH475986A (de) | 1969-07-31 |
| FI48587B (pt) | 1974-07-31 |
| YU33070B (en) | 1976-03-31 |
| AT267528B (de) | 1969-01-10 |
| NL6618360A (pt) | 1967-07-03 |
| GB1120700A (en) | 1968-07-24 |
| SE305218B (pt) | 1968-10-21 |
| YU155572A (en) | 1975-08-31 |
| FI48587C (fi) | 1974-11-11 |
| CS152273B2 (pt) | 1973-12-19 |
| YU32697B (en) | 1975-06-30 |
| AT266136B (de) | 1968-11-11 |
| DE1695003A1 (de) | 1970-09-10 |
| US3511842A (en) | 1970-05-12 |
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